Category: 104750-60-9

Synthetic Route of 104750-60-9, The chemical industry reduces the impact on the environment during synthesis 104750-60-9, name is 2-Bromo-1-(methoxymethoxy)-4-methylbenzene, I believe this compound will play a more active role in future production and life.

The bromination of p- cresol, carried out via the method of Narender, et al.,3 was followed by MOM protection 4 (96% yield over two steps). A solution of bis(pinacolato)diborane (2.5 g), dioxane (40 mL), KOAc (2.5 g) and the aryl bromide (6.5 mmol) was purged with nitrogen before Pd(dppf)Cl2 (0.47 g) was added. The mixture was refluxed overnight. Silica chromatography (gradient to 20%) EtOAc/hexanes) gave the boronate ester (1.93 g), which was dissolved in acetone (20 mL) and treated with a solution of Oxone (4 g) in H20 (20 mL). After 10 min, NaHS03 was added and the resulting solution was extracted with EtOAc. Silica chromatography (gradient up to 15% EtOAc/hexanes) gave 2-(methoxymethoxy)-5-methylphenol (0.578 g, 53% over two steps). The diaryl ether was prepared from the phenol and appropriate 4-fluorobenzalde using General Procedure D. Silica chromatography (gradient up to 40% EtOAc/hexanes) gave the intermediate aldehyde (481 mg, 47%). The oxidation was followed by MOM cleavage with cone. HC1 (0.25 mL) in 50% THF/iPrOH (10 mL) to yield 18o (391 mg, 89% over two steps). 1H NMR (CDC13) delta 7.73-7.66 (m, 2H), 6.99-6.85 (m, 3H), 6.76 (s, 1H), 3.97 (s, 3H), 2.24 (s, 3H).

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, 2-Bromo-1-(methoxymethoxy)-4-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RESEARCH TRIANGLE INSTITUTE; CARROLL, Frank, I.; THOMAS, James, B.; NAVARRO, Hernan, A.; MASCARELLA, S., Wayne; RUNYON, Scott, P.; JIN, Chunyang; KORMOS, Chad, M.; WO2013/86496; (2013); A2;,
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Reference of 104750-60-9, 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. 104750-60-9, name is 2-Bromo-1-(methoxymethoxy)-4-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 4-(2-hydroxy-5-methylphenoxy)-3-methoxybenzoic acid (18o). The bromination of p-cresol, carried out via the method of Narender, et al.,3 was followed by MOM protection4 (96% yield over two steps). A solution of bis(pinacolato)diborane (2.5 g), dioxane (40 mL), KOAc (2.5 g) and the aryl bromide (6.5 mmol) was purged with nitrogen before Pd(dppf)Cl2 (0.47 g) was added. The mixture was refluxed overnight. Silica chromatography (gradient to 20% EtOAc/hexanes) gave the boronate ester (1.93 g), which was dissolved in acetone (20 mL) and treated with a solution of Oxone (4 g) in H2O (20 mL). After 10 min, NaHSO3 was added and the resulting solution was extracted with EtOAc. Silica chromatography (gradient up to 15% EtOAc/hexanes) gave 2-(methoxymethoxy)-5-methylphenol (0.578 g, 53% over two steps). The diaryl ether was prepared from the phenol and appropriate 4-fluorobenzalde using General Procedure D. Silica chromatography (gradient up to 40% EtOAc/hexanes) gave the intermediate aldehyde (481 mg, 47%). The oxidation was followed by MOM cleavage with conc. HCl (0.25 mL) in 50% THF/iPrOH (10 mL) to yield 18o (391 mg, 89% over two steps). 1H NMR (CDCl3) delta 7.73-7.66 (m, 2H), 6.99-6.85 (m, 3H), 6.76 (s, 1H), 3.97 (s, 3H), 2.24 (s, 3H).

The synthetic route of 2-Bromo-1-(methoxymethoxy)-4-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESEARCH TRIANGLE INSTITUTE; Carroll, Frank I.; Thomas, James B.; Navarro, Hernan A.; Mascarella, S. Wayne; Runyon, Scott P.; Jin, Chunyang; Kormos, Chad M.; (20 pag.)US9512105; (2016); B2;,
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Ether | (C2H5)2O – PubChem

Reference of 104750-60-9, A common heterocyclic compound, 104750-60-9, name is 2-Bromo-1-(methoxymethoxy)-4-methylbenzene, molecular formula is C9H11BrO2, 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.

2-Bromo-1-(methoxymethoxy)-4-methylbenzene (2.3 g, 9.95 mmol) from Example I-122A was dissolved in tetrahydrofuran (39.8 mL), and Q-Phos (1,2,3,4,5-pentaphenyl-1′-(di-tert-butylphosphino)ferrocene) (0.141 g, 0.199 mmol) and bis(dibenzylideneacetone)palladium (0.114 g, 0.199 mmol) were added. The reaction was sparged with nitrogen 10 minutes. A solution of freshly-prepared (1-(methoxycarbonyl)cyclopropyl)zinc(II) bromide (45.2 mL, 19.91 mmol) in tetrahydrofuran was added dropwise. The reaction mixture was stirred at 50 C. for 30 minutes and at 45 C. for 15 hours. The reaction was cooled to ambient temperature and quenched with saturated aqueous ammonium chloride (40 mL). The mixture was diluted with methyl tert-butyl ether. The aqueous layer was extracted once with methyl tert-butyl ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude material was purified by flash column chromatography, eluting with 0-20% ethyl acetate/heptanes to provide the title compound. 1H NMR (501 MHz, chloroform-d) delta ppm 7.06-6.99 (m, 2H), 6.97 (d, J=8.1 Hz, 1H), 5.16 (s, 2H), 3.60 (s, 3H), 3.45 (s, 3H), 2.28 (s, 3H), 1.63-1.57 (m, 2H), 1.12 (q, J=4.1 Hz, 2H)+

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; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; Desroy, Nicolas; Gfesser, Gregory A.; Housseman, Christopher Gaetan; Kym, Philip R.; Liu, Bo; Mai, Thi Thu Trang; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Picolet, Olivier Laurent; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; (189 pag.)US2019/77784; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 104750-60-9, The chemical industry reduces the impact on the environment during synthesis 104750-60-9, name is 2-Bromo-1-(methoxymethoxy)-4-methylbenzene, I believe this compound will play a more active role in future production and life.

A solution of 9-bromoanthracene (0.67 g, 2.6 mmol, 1.2 eq) in dry Et2O (13 mL) under N2 was cooled to -30 C and “Buli (1.6 M in hexane, 1.6 mL, 2.6 mmol, 1.2 eq) was added dropwise. The solution was stirred for 20 min. at -30 C followed by dropwise addition of ZnCl2 (0.50 M in THF, 5.2 mL, 2.6 mmol, 1.2 eg). The reaction was stirred and warmed to RT over 30 min. The volatiles were removed under N2 purge and the residue was redissolved in 3:1 THF/NMP (11 mL). The MOM-protected bromophenol (2.2 mmol, 1.0 eg) and Pd(PtBu3)2 (22 mg, 44 mumol, 4 mol %) were added and the reaction was heated to 100 C for 2 h. The reaction was cooled to RT and the THF was removed. The residue was diluted with CH2C12, washed with 1 M HCI, and dried over Na2S04. The crude material was purified by flash chromatography. Synthesized by General Method Cl. Purified by flash chromatography (Biotage FLASH 40S KP-Sil silica, 0-5% EtzO/hexanes) to yield 0.59 g (84%) of 31 as a white solid. ?H NMR (CDCl3,300 MHz): 8.48 (s, 1H), 8.03 (d, J= 8.7 Hz, 2H), 7.65 (dd, J= 8.7 Hz, J = 0.6 Hz, 2H), 7.50-7.20 (m, 6H), 7.09 (d, J= 1.8 Hz, 1H), 4.84 (s, 2H), 3.00 (s, 3H), 2.38 (s, 3H).

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, 2-Bromo-1-(methoxymethoxy)-4-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYMYX TECNOLOGIES, INC; WO2005/108406; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem