Category: 450-88-4

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 450-88-4 name is 1-Bromo-4-fluoro-2-methoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 450-88-4

Intermediate Example Int20.014-(4-bromo-3-methoxyphenoxy)-1 -methylpiperidine To a stirred suspension of sodium hydride (1.76 g; 60% w/w sodium hydride in oil) in DMF (55 mL) was added 1 -methylpiperidin-4-ol (3.37 g) at 0 C. The mixture was stirred at room temperature for 30 minutes. 1 -bromo-4-fluoro-2- methoxybenzene (3.0 g) was added and the mixture was stirred at 100 C for 1 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Aminophase-silica- gel chromatography gave 3.65 g of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-fluoro-2-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; KOSEMUND, Dirk; SCHIROK, Hartmut; BADER, Benjamin; LIENAU, Philip; WENGNER, Antje Margret; BRIEM, Hans; HOLTON, Simon; SIEMEISTER, Gerhard; PRECHTL, Stefan; KOPPITZ, Marcus; STOeCKIGT, Detlef; PRIEN, Olaf; WO2011/157688; (2011); A1;,
Ether – Wikipedia,
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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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., Quality Control of 1-Bromo-4-fluoro-2-methoxybenzene

10504] Under a nitrogen atmosphere, into a reaction vessel equipped with a dropping flannel were added 1.00 g of 2-bromo-5-fluoroanisole and 20 mE of tetrahydrofuran. The resultant solution was cooled down to -78 C., then, 3.0 mE of n-butyllithium (1.62 Mlhexane solution) was dropped. The resultant mixture was stirred at the same temperature for 3 hours, then, a solution obtained by dissolving 1.00 g of chlorodicyclopentylphosphine in 13 ml of tetrahydroffiran was dropped at -78 C. The resultant mixture was stirred at room temperature for 3 hours. The resultant reaction mixture was concentrated, to obtain 1.75 g of a mixture in the form of viscous liquid containing dicyclopentyl(4-fluoro-2-methox- yphenyl)phosphine.

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; Sumitomo Chemical Company, Limited; ODA, Seiji; KAMIKAWA, Takashi; US2015/322101; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 450-88-4, These common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, 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.

The solution of anisole of formula 2 (Scheme 6) (61 .5 g, 0.3 mol) in 1 ,2-dichloroethane (DCE) (600 mL) was cooled to -10 C and AICI3 was added in portions, maintaining the temperature below 2 C. The solution was then cooled to -5 C and acetyl chloride (56 mL, 0.79 mol) was added dropwise maintaining the internal temperature below 5 C. The reaction mixture was aged for 1 hour at 0 C. At this time HPLC showed no more starting material. The reaction mixture was quenched into ice (600 g) at a rate such that the internal temperature remained below 20 C. The resulting mixture was extracted with EtOAc (400 mL) and the organic phase then washed with 1 HCL (400 mL), saturated NaHC03 (400 mL) and brine (200 mL), dried over Na2S0 and filtered. The solvent was removed under reduced pressure to give acetophenon of formula 3 (Scheme 6) as a white solid (74.0 g, 100%): mp 1 13-1 17 C; H NMR (CDCI3) 5 2.59 (d, J = 5.1 Hz, 3H), 3.95 (s, 3H), 6.64 (d, J = 12.5 Hz, 1 H), 8.13 (d, J = 7.9 Hz, 1 H).

The synthetic route of 450-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., SDS of cas: 450-88-4

To a mixture of magnesium (0.79 g, 32.5 mmol) and lithium chloride (1.52 g, 35.80 mmol) in THF (33 ml) at room temperature was added 1-bromo-4-fluoro-2-methoxybenzene (3.13 mL, 24.39 mmol) and the reaction was stirred at 70 C for 1.5 hr. The reaction was then cooled to 0 C, and Fe(acac)3 (0.574 g, 1.63 mmol) was added. After 1 minute, allyl chloride (1.33 mL, 16.26 mmol) was added and the reaction was stirred at 0 C for 30 min. The mixture was warmed to room temperature over 1 hr and was heated at 70 C overnight. The reaction was cooled and diluted with petroleum ether (100 mL). The reaction was then quenched by the addition of a saturated NH4Cl solution (100 mL). The mixture was filtered through a Celite pad and the layers were separated. The aqueous layer was extracted with petroleum ether (2 x 100 mL) and the combined organic phases were dried over Na2SO4 and carefully concentrated (25 C, 250 mbar). The residue was purified by Isco chromatography (100% pet ether as the eleuent) to provide (E,Z)-4-fluoro-2- methoxy-1-(prop-1-en-1-yl)benzene (2.25 g, 83 % yield) as a colorless oil. This mixture was approximately a 3:1 mixture of E and Z isomers with a trace of the allyl isomer present. This material was used directly in the next step.1H NMR (400 MHz, CDCl3) delta 7.31 (dd, J = 8.3, 6.8 Hz, 1H), 6.65- 6.53 (m, 3H), 6.14 (dq, J = 15.8, 6.6 Hz, 1H), 3.82 (s, 3H), 1.88 (dd, J = 6.6, 1.7 Hz, 3H).19F NMR (376 MHz, CDCl3) delta -113.30.

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; DOW AGROSCIENCES LLC; BUCHAN, Zachary A.; LU, Yu; JONES, David M.; MEYER, Kevin G.; YAO, Chenglin; (110 pag.)WO2018/44996; (2018); A1;,
Ether – Wikipedia,
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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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Bromo-4-fluoro-2-methoxybenzene

A mixture of 1 -bromo-4-fluoro-2-methoxybenzene (CAS No. [450-88-4]; 10.0 g, 48.8 mmol) in concentrated sulfuric acid (50 ml.) was cooled to 0 C and treated dropwise with a freshly prepared mixture of fuming nitric acid (1.05 eq., 2.1 ml_, 51 mmol) and concentrated sulfuric acid (1.85 eq., 4.8 ml_, 90 mmol). The reaction mixture was stirred at 0 C for 30 minutes and poured in small portions on ice water. The formed precipitate was filtered off, washed with cold water and kept. The filtrate was extracted with ethyl acetate and the organic layer combined with the isolated precipitation. The organic layer was dried with sodium sulfate and concentrated in vacuo. The obtained material was purified by flash chromatography (Si02-hexane/ ethyl acetate) to give the title compound (5.88 g, 44%). 1H-NM (400MHz, DMSO-de): delta [ppm] = 4.00 (s, 3H), 7.44 (d, 1 H), 8.40 (d, 1 H).UPLC- UPLC-MS (ESI-): [M – H]” = 248/250; Rt = 1.17 min (Br isotope pattern; Method E).

The synthetic route of 450-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; PANKNIN, Olaf; ZIMMERMANN, Katja; NEUHAUS, Roland; (162 pag.)WO2017/5674; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., Product Details of 450-88-4

Step 1. 3-Bromo-6-fluoro-2-methoxybenzaldehyde 1.6 M Solution of n-butyllithium in hexanes (3.35 mL, 5.36 mmol) was added dropwise to a solution of N,N-diisopropylamine (0.960 mL, 6.85 mmol) in tetrahydrofuran (10 mL) at -78 C. and the resultant reaction mixture was stirred at -78 C. for 10 min. A solution of 1-bromo-4-fluoro-2-methoxybenzene (1.0 g, 4.9 mmol) in tetrahydrofuran (2 mL) was added to the reaction mixture dropwise at -78 C. and the reaction mixture was stirred at -78 C. for 1 h. N,N-dimethylformamide (0.412 mL, 5.32 mmol) was added to the reaction mixture dropwise at -78 C. and the reaction mixture was stirred at -78 C. for 1 h. Reaction mixture was quenched with saturated ammonium chloride, warmed to 20 C., and diluted with ether and 1M aqueous solution of HCl. Layers were separated and the aqueous layer was and re-extracted with ether. The combined organic layers were washed with brine, dried with magnesium sulfate, filtered, and concentrated in vacuo to give a crude residue. Purification by flash column chromatography (100% hexanes to 30% EtOAc/hexanes) gave the desired product (727 mg, 64%) as a yellow solid. LCMS calculated for C8H7BrFO2 (M+H)+: m/z=233.0, 235.0. found: 233.0, 234.8.

The synthetic route of 450-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; Yue, Eddy W.; Combs, Andrew P.; Douty, Brent; US2015/148342; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, 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 450-88-4, category: ethers-buliding-blocks

4-Fluoro-2-methoxybenzenethiol To a suspension of 2-bromo-5-fluoroanisole (2.00 g, 9.755 mmol) and elemental sulphur (0.468 g, 14.632 mmol) in dry THF (50 mL) was slowly added tert-butyl lithium in pentane (1.7 M, 12.6 mL, 21.46 mmol) AT-78C. The resulting suspension was allowed to stir at-78C for 60 mins before being poured onto saturated ammonium chloride solution (80 mL) and product extracted with diethyl ether (100 mL). The organic phase was washed with aqueous hydrochloric acid (2 N, 40 mL), with the resulting organic phase being dried (MgSO4) and the solvent evaporated in vacuo to give a pale yellow oil. This was treated to a pad of silica gel, eluting with hexane: ethyl acetate [95: 5] to give a pale yellow oil (1.50 g, 68%). ON (300 MHz, CDC13) 7.20 (1H, dd, Ar), 6.65-6. 55 (2H, d, AR), 3.90 (3H, s, OCH3), 3.68 (1H, s, SH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-fluoro-2-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/43903; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 450-88-4, 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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate Example Int17.031 -(4-bromo-3-methoxyphenyl)-4-ieri-butylpiperazineTo a stirred solution of 1 -tert-butylpiperazine (5.0 g) in THF (25 mL) was added n-butyllithium in hexanes (4.2 mL, c = 2.5 M) at -78C. The solution was stirred for 30 min at 0C. A solution of 1 -bromo-4-fluoro-2-methoxybenzene (1.44 g) in THF (2 mL) was added at -78 C and the reaction mixture was allowed to warm up to 0 C over 3 h. The mixture was stirred at 0 C for 2 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Aminophase-silica-gel chromatography gave 490 mg of the title compound.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-fluoro-2-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; SCHULZE, Volker; KOSEMUND, Dirk; WENGNER, Antje, Margret; SIEMEISTER, Gerhard; STOeCKIGT, Detlef; LIENAU, Philip; BRIEM, Hans; WO2012/160029; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 450-88-4, A common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, molecular formula is C7H6BrFO, 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.

Intermediate Example Int10.101 -bromo-2-methoxy-4-(methy Isu Ifany l)benzeneTo a stirred solution of 1 -bromo-4-fluoro-2-methoxybenzene (4.0 g) in DMF (40 mL) was added sodium methanethiolate (2.76 g). The mixture was stirred at r.t. for 30 minutes and at 85 C for 2 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 280 mg of the title compound.1H-NMR (400MHz, DMSO-d6): delta [ppm]= 2.46 (s, 3H), 3.82 (s, 3H), 6.74 (dd, 1 H), 6.91 (d, 1 H), 7.44 (d, 1 H). 1 -bromo-2-methoxy-4-(methy Isu Ifany l)benzene To a stirred solution of 1 -bromo-4-fluoro-2-methoxybenzene (10.0 g) in DMF (100 mL) was added sodium methanethiolate (4.44 g). The mixture was stirred at 65C for 2 h. The mixture was cooled to 0 C and methyl iodide (4.55 mL) was added. The mixture was stirred at r.t. for 1 h and further sodium methanethiolate (4.44 g) was added. The mixture was stirred at 65C for 1 h. The mixture was cooled to 0 C and methyl iodide (4.55 mL) was added. The mixture was stirred at r.t. for 1 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 6.2 g of the title compound as a 2: 1 mixture with the starting material. The mixture was used for the next step without purification.

The synthetic route of 450-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; SCHULZE, Volker; KOSEMUND, Dirk; WENGNER, Antje, Margret; SIEMEISTER, Gerhard; STOeCKIGT, Detlef; LIENAU, Philip; SCHIROK, Hartmut; BRIEM, Hans; WO2012/143329; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 450-88-4,Some common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, molecular formula is C7H6BrFO, 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.

Description 18; : 3-Bromo-6-fluoro-2-(methyloxy)benzaldehyde (D18)To a solution of diisopropylamine (6.89 g, 9.6 ml_, 68.3 mmol) in THF (100 ml.) at -78 C was added n-butyl lithium (33.5 ml. of 1.6 M solution in hexane, 53.6 mmol) over 3 mins. After stirring at -78 C for 10 mins, 2-bromo-5-fluroanisole (10 g, 48.8 mmol) in THF (20 ml.) was added dropwise over 15 mins. After completion of the addition, the mixture was stirred at -78 C for 1 hr and then DMF (3.91 g, 4.12 ml_, 53.6 mmol) was added dropwise over 3 mins and stirring was continued at -78 C for 45 mins. Saturated NH4CI solution was added and the mixture allowed to each room temperature. Diethyl ether and 2M HCI were added, the product was extracted into diethyl ether and the combined extracts were washed with brine, dried and evaporated. Chromatography on silica gel followed by trituration of the product with diethyl ether gave the title compound (D18) as a yellow solid (6.84 g) NMR (deltaH), (CDCI3): 3.97 (3H, s), 6.90 (1 H, m), 7.76 (1 H, dd, J = 5.9, 11.0 Hz), 10.34 (1 H, s).

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/107455; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem