Category: 14804-31-0

Related Products of 14804-31-0,Some common heterocyclic compound, 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, molecular formula is C8H9BrO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a solution of compound 1a-e (10.0 mmol,1.0 eq) in anhydrousTHF (20 mL) was slowly added n-BuLi (6 mL of 2.5 M solution inhexane, 15.0 mmol, 1.5 eq) at 78 C. The mixture was stirred for1 h and triisopropyl borate (50.0 mmol, 5.0 eq) was added by syringe.The solutionwas stirred for another 1 h and allowed towarmto 25 C overnight. The reactionwas cooled to 0 C, followed by thesequential addition ofwater (5 mL) and 2N HCl (5 mL). After 10 min,an additional 35 mL of 2N HCl was added and the mixture wasfurther stirred for 30 min. The mixture was extracted with ethylacetate (20 mL * 3) and the combined organic layers wereconcentrated to a thick oil under reduced pressure. Crystallizationwith cold hexane yielded a white solid.

The synthetic route of 14804-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sang, Yali; Han; Pannecouque, Christophe; De Clercq, Erik; Zhuang, Chunlin; Chen; European Journal of Medicinal Chemistry; vol. 182; (2019);,
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Electric Literature of 14804-31-0, The chemical industry reduces the impact on the environment during synthesis 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 109; Preparation of 2-Amino-5-(4-methoxy-3-methyl phenyl)-3-methyl-5-(2-phenylpyridin-4-yl)-3,5-dihydro-4H-imidazol-4-one; Step a) [(4-Methoxy-3-methylphenyl)ethynyl](trimethyl)silane; A solution of 4-bromo-1-methoxy-2-methylbenzene (6.702 g) in toluene was treated with tetrakis(triphenylphosphie)palladium (0) (1.15 g), followed by diisopropylamine (23 mL), trimethylsilyl acetylene (4.7 mL) and copper iodide (I) (0.127 g). The reaction was heated at 45 C. in nitrogen atmosphere overnight and evaporated to dryness. The resultant residue was applied on a large silica pad and eluted with hexane:ethyl acetate (2:1). The elute was evaporated to dryness to give the silane intermediate as a brown oil (7.167 g). The compound was characterized by LCMS analysis. LCMS Conditions: HP 1100 HPLC system; Waters Xterra MS C18, 2 mm (i.d.)×50 mm (length), 3.5 um column, set at 50 C.; Flow rate 1.0 mL/min; Solvent A: 0.02% NH4OH in water; Solvent B 0.02% NH4OH in ACN; Gradient: Time O: 10% B; 2.5 min 90% B; 3 min 90% B; Sample concentration: 2.0 mM; Injection volume: 5 uL; Detection: 220 nm, 254 nm DAD

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-1-methoxy-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wyeth; US2007/4730; (2007); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 14804-31-0

n-Butyllithium (2.5 M in hexanes, 60 mL, 150.0 mmol) was added dropwise to a solution of 4-bromo-1-methoxy-2-methylbenzene (27.78 g, 138.2 mmol) in THF (300 mL) at-78 C. The mixture was stirred at -78 C for 1 h and then added dropwise to a solution of ethyl 4-oxocyclohexanecarboxylate (22.34 g, 131.3 mmol) in THF (300 mL) at -78 C. The mixture was stirred at -78 C for 2 h, added to sat?d NH4C1 (600 mL) and then extracted with EtOAc (2×600 mL). The combined organic extracts were washed with water (400 mL), washed with brine (400 mL), dried (Na2504), filtered, concentrated, and purified by silica gel chromatography (petroleum ether/EtOAc = 10/1) to give ethyl 4-hydroxy-4-(4-methoxy-3 – methylphenyl)cyclohexanecarboxylate (18.9 g, 45%) as a yellow oil. ?H NIVIR (400 MHz, DMSO): 7.11-7.26 (m, 2H), 6.75-6.84 (m, 1H), 4.59-4.64 (m, 1H), 3.98-4.11 (m, 2H), 3.72 (s, 3H), 2.25-2.39 (m, 1H), 2.07-2.13 (s, 3H), 1.77-1.93 (m, 3H), 1.42-1.75 (m, 5H), 1.11- 1.23 (m, 3H); LCMS: 275.2 [M-OH].

The synthetic route of 14804-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (169 pag.)WO2018/170166; (2018); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 14804-31-0

After starting the Grignard reaction by adding 25.0 ml 4-bromo2-methyl-anisole to a mixture of 30.2 g (1.24 mol) magnesium turnings and 650 ml THF, 150 ml 4-bromo2-methylanisole (total: 175.0 ml were added at a pace sufficient to maintain reflux temperature. The reaction mixture was heated to reflux for additional 5 h, cooled to r.t. and dropped at 0 C. within 1 h to a stirred solution prepared by mixing 904 g (500 ml, 4.19 mol) 1,4-dibromo-butane in 1000 ml THF with a freshly prepared solution of 1.28 g (60.0 mmol) LiCl and 4.00 g (29.8 mmol) Cu(II)Cl2 in 140 ml THF. Stirring was continued for 12 h at r.t. followed by the addition of 400 ml of a 20% ammonium chloride solution and 200 ml ethyl acetate. The water phase was extracted twice with 250 ml ethyl acetate, all organic phases were combined, dried over sodium sulphate and evaporated. The resulting oil was fractionated by vacuum distillation. Yield: 226.3 g (71%), b.p. 131-134 C./0.01 mbar. 1H-NMR(400 MHz, D6-DMSO): delta=1.60(quintet, 2H, C2-CH2-Ph), 1.82(quintet, 2H, C2-CH2-Br), 2.23(s, 3H, CH3), 2.51(t, 2H, CH2-Ph), 3.55(t, 2H, CH2-Br), 3.70(s, 3H, OCH3), 6.67d, 1H, 5-H), 6.72(s, 1H, 3-H), 7.01(d, 1H, 6-H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 14804-31-0.

Reference:
Patent; Hofmeister, Thomas; Reiff, Ulrike; von Hirschheydt, Thomas; Voss, Edgar; US2006/69095; (2006); A1;,
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Related Products of 14804-31-0,Some common heterocyclic compound, 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, molecular formula is C8H9BrO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(RS)-1-(3-Bromo-2-fluorophenyl)-1-(4-methoxy-3-methylphenyl)ethanol Magnesium turnings (981 mg) and a crystal of iodine were suspended in tetrahydrofuran (10 mL) at room temperature. To this was added ~5 mL of a solution of 4-bromo-2-methylanisole (7.1 g) in tetrahydrofuran (100 mL). The mixture was then heated at reflux until initiation (colour change from brown to colourless ~15-30 min) after which time the heat was removed. The remaining 4-bromo-2-methylanisole solution was added dropwise to maintain a gentle reflux and the resultant mixture was then heated at reflux for 2 h. Upon cooling to room temperature, a solution of 1-(3-bromo-2-fluorophenyl)-ethanone (7.3 g) in tetrahydrofuran (100 mL) was added dropwise, again maintaining a gentle reflux and this was then heated at reflux for 2 h before being allowed to cool to room temperature. The mixture was then poured onto ice-water (400 mL) and the solvent removed by evaporation. The product was extracted with ethyl acetate (3*100 mL), dried over sodium sulfate and the solvent removed by evaporation to yield a yellow oil. Purification by flash chromatography on silica (20:1-5:1 hexanes/ethyl acetate) yielded (R,S)-1-(3-bromo-2-fluorophenyl)-1-(4-methoxy-3-methylphenyl)ethanol as a yellow oil (6.37 g, 56%). 1H NMR (CDCl3): 1.94 (3H, s, ArCH3), 2.17 (3H, s, ArCH3), 3.80 (3H, s, ArOCH3), 6.75 (1H, d, Ar), 7.00-7.16 (3H, m, Ar), 7.47 (1H, t, Ar), 7.63 (1H, t, Ar).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-methoxy-2-methylbenzene, its application will become more common.

Reference:
Patent; Andreini, Matteo; Gabellieri, Emanuele; Guba, Wolfgang; Marconi, Guido; Narquizian, Robert; Power, Eoin; Travagli, Massimiliano; Woltering, Thomas; Wostl, Wolfgang; US2009/209529; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 14804-31-0, A common heterocyclic compound, 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, molecular formula is C8H9BrO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(RS)-1-(3-Bromo-4-chlorophenyl)-1-(4-methoxy-3-methylphenyl)-ethanol 5-Bromo-2-methoxytoluene (6.4 g, 0.032 mol) was dissolved in tetrahydrofuran (100 mL) and 5 mL of the solution was added to a stirred mixture of magnesium turnings (0.90 g, 0.037 mol) and iodine (a catalytic amount) in tetrahydrofuran (10 mL). The mixture was heated to vigorous reflux until some of the iodine colour was lost. The flask was removed from the heat and the remainder of the bromide was added so as to maintain a gentle reflux. The flask was then returned to the heat and stirred at reflux for 2 hours. The flask was removed from the heat and a solution of 1-(3-bromo-4-chlorophenyl)-ethanone (7.1 g, 0.030 mol) in tetrahydrofuran (100 mL) was added so as to maintain a gentle reflux. The reaction mixture was returned to the heat and stirred at reflux for 3 hours then cooled to room temperature and poured into ice-water (300 mL). The mixture was stirred for 5 minutes then concentrated to remove tetrahydrofuran. The aqueous residue was diluted with aqueous ammonium chloride (100 mL), extracted with ethyl acetate (3*200 mL) and the combined organic extracts were washed with water (100 mL) and brine (100 mL), dried (sodium sulfate) and concentrated to give the crude product as a red oil which was purified by flash chromatography (5 to 10% ethyl acetate/hexane) to give the desired alcohol as a bright yellow oil (6.7 g, 71%). 1H NMR (300 MHz; CDCl3) 7.72 (1H, d, J2.1, Ar), 7.35 (1H, d, J 8.5, Ar), 7.23-7.13 (3H, m, Ar), 6.76 (1H, d, J 8.5, Ar), 3.82 (3H, s, OMe), 2.19 (3H, s, Me), 2.11 (1H, s, OH), 1.88 (3H, s, Me).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Andreini, Matteo; Gabellieri, Emanuele; Guba, Wolfgang; Marconi, Guido; Narquizian, Robert; Power, Eoin; Travagli, Massimiliano; Woltering, Thomas; Wostl, Wolfgang; US2009/209529; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 14804-31-0, Recommanded Product: 14804-31-0

General procedure: 25-ml RB was charged with 4-iodo anisole (1.0 mmol), phenyl boronic acid (1.5 mmol), GO-PMMA-Pd catalyst (0.3 mol %), K2CO3 (1 mmol), TBAB (10 mol %) and 2 ml water. The mixture was allowed to stir at 90 C for an appropriate time (Table 1) and the extent of the reaction was monitored by thin layer chromatography (TLC). After the completion of the reaction, the reaction mixture was extracted by ethyl acetate (2¡Á25 mL) and washed with water repeatedly. The catalyst was filtered off and washed several times with ether and water (1:1) until no significant product was obtained in the wash. The recoverd catalyst was reused for the next coupling experiment. The reaction mixture was dried over anhydrous Na2SO4, concentrated in vacuum and purified by column chromatography on silica gel 60-120 mesh using petroleum ether as eluent to obtain pure product. The catalyst recoverd after 5th run was subjected to ICP-AES for Pd content analysis. The isolated products were analysed by 1H NMR and 13C NMR spectroscopy.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-1-methoxy-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Basak, Puja; Ghosh, Pranab; Synthetic Communications; vol. 48; 19; (2018); p. 2584 – 2599;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Step b: To a degassed (argon) solution of 3b (10.0 g, 49.7 [MMOL)] in DMF (310 mL) was added bis (pinacolato) diborane (13.9 g, 54.7 [MMOL), KOAC] (14.2 g, 149 [MMOL)] and [PDCL2DPPF] (1: 1 complex with [CH2CI2,] 4.87 g, 5.96 [MMOL).] The reaction mixture was heated to 80 C for 24 h then was cooled to 25 [C.] 4-Bromobenzeneacetic acid (21.4 g, 99.5 [MMOL),] aqueous 2 M [NA2CO3 SOLUTION] (124 mL, 248 [MMOL)] and additional [PDCI2DPPF] (1: 1 complex with [CH2CI2,] 4.87 g, 5.96 [MMOL)] were added to the mixture. The reaction mixture was heated to [80 C] for 12 h. The cooled mixture was acidified with aqueous 4 N HCI solution and extracted with EtOAc (3 x). The combined organic layers were successively washed with water (2 x) and brine, dried [(MGS04),] filtered and concentrated under reduced pressure. The crude resulting acid was dissolved in [ET2O] and was treated with excess ethereal [CH2N2] solution (ca. 0.6 M). The mixture was concentrated under reduced pressure. The residue was purified by flash chromatography (hexane/EtOAc, 19/1) to give 3c (4.25 g, 32% yield) as a pale yellow solid.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BOEHRINGER INGELHEIM (CANADA) LTD.; WO2004/26875; (2004); A1;,
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Ether | (C2H5)2O – PubChem

Application of 14804-31-0,Some common heterocyclic compound, 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, molecular formula is C8H9BrO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Reference Example 595-[4-(4-methoxy-3-methylphenyl)piperazin-1-yl]-2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-oneSodium t-butoxide (999 mg, 10.4 mmol) was added to a mixture of toluene (18 mL) containing 2,2,4,6,7-pentamethyl-5-piperazin-1-yl-1-benzofuran-3(2H)-one (1.00 g, 3.47 mmol) synthesized in Reference Example 58, 4-bromo-2-methylanisole (2.09 g, 10.4 mmol), palladium acetate (39 mg, 0.174 mmol) and BINAP (325 mg, 0.522 mmol), and the mixture was stirred under heated reflux for 15 hours. After cooled to room temperature, the reaction solution was diluted with water and extracted using ethyl acetate. The organic layer was washed with saturated saline, and then dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5 to 85:15). Crystallization was performed using ethyl acetate-hexane to give 320 mg of the title compound (yield: 23%).Melting point: 129-131 C.1H-NMR (CDCl3): delta1.43 (6H, s), 2.18 (3H, s), 2.22 (3H, s), 2.35 (3H, s), 2.61 (3H, s), 3.02-3.42 (8H, m), 3.80 (3H, s), 6.74-6.84 (2H, m), 6.85-6.89 (1H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-methoxy-2-methylbenzene, its application will become more common.

Reference:
Patent; Tsukamoto, Tetsuya; Wakabayashi, Takeshi; Ohra, Taiichi; US2010/234357; (2010); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 4-Bromo-1-methoxy-2-methylbenzene

4-[1-(3-Bromo-phenyl)-vinyl]-1-methoxy-2-methyl-benzene Tetrahydrofuran (5 mL) was added to magnesium turnings (330 mg, 13.56 mmol) in a dried apparatus consisting of 250 mL 3-necked flask, addition funnel and reflux condenser. Then 5 mL of a solution of 4-bromo-2-methylanisole (2.5 g, 12.43 mmol) in tetrahydrofuran (15 mL) was added, followed by a drop of bromine. The exothermic reaction started instantaneously, and the 4-bromo-2-methylanisole solution was added at such a rate to maintain gentle reflux of the reaction mixture (25 min). After complete addition, the light-brown hazy Grignard solution was stirred for another 2 h at 40 C. The mixture was then cooled to 0 C. and a solution of 3-bromoacetophenone (1.42 mL, 11.3 mmol) in tetrahydrofuran (15 mL) was added dropwise over 30 min. After the addition was complete, the mixture was stirred overnight, followed by cooling in an ice bath and careful quenching with 0.5 N cold HCl. After further dilution with ethyl acetate (100 mL) and water (100 mL), the layers were separated and the aqueous layer extracted once more with ethyl acetate (50 mL). The organic layer was dried (magnesium sulfate), filtered and evaporated under reduced pressure. The residual material (tertiary alcohol) was dissolved in a mixture of acetic acid/sulfuric acid (4 mL of acetic acid, 0.12 mL of sulfuric acid) and the reaction mixture was stirred for 3 h at room temperature; then it was examined by LC-MS which showed the complete formation of desired product. The solution was quenched with ice and dichloromethane (20 mL) was added. The two phases formed and were separated. The organic layer was washed with a saturated solution of sodium bicarbonate and brine. It was then dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. Crude was purified by flash chromatography eluding with cyclohexane. 1.9 g of desired product was obtained as colorless oil (Yield: 55%). Mass (calculated) C16H15BrO [303] M-H+ not observed LC Rt=3.05 min (5 min method) 1H-NMR (CDCl3): 2.23 (s, 3H); 3.86 (s, 3H); 5.35 (s, 1H); 5.43 (s, 1H); 6.80 (m, 1H); 7.13 (m, 2H); 7.21 (m, 1H); 7.28 (m, 1H); 7.46 (m, 1H); 7.53 (m, 1H)

The synthetic route of 14804-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Andreini, Matteo; Gabellieri, Emanuele; Guba, Wolfgang; Marconi, Guido; Narquizian, Robert; Power, Eoin; Travagli, Massimiliano; Woltering, Thomas; Wostl, Wolfgang; US2009/209529; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem