Category: 31804-36-1

Synthetic Route of 31804-36-1, These common heterocyclic compound, 31804-36-1, name is 1-Bromo-3-methoxy-2-methylbenzene, 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.

To a solution of intermediate 139 (2.5 g, 12.4 mmol) in THF (30 mL) at -70 C was added n-BuLi (1.6 M in hexane) (7.8 mL, 12.4mmol) dropwise over 5 min by syringe along the wall of the flask. After adding, the reaction was stirred at this temperature for 30 min. Then the resulting solution was added into a solution of (S)-tert-butyl 1,6- dioxohexahydropyrrolo[l,2-a]pyrazine-2(lH)-carboxylate (2.0 g, 12 mmol) in THF (30 mL). After stirred at -70C for 5 min, the reaction mixture was quenched with saturated NH4CI and extracted with EtOAc (2 x 20 mL), washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to give the title compound (2 g, yield : 45 %); m/z (ES+) : 377 [M+H]+.

The synthetic route of 31804-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEO PHARMA A/S; BLADH, Haakon; FELDING, Jakob; ZHOU, Ding; CAI, Zhen-wei; SØRENSEN, Morten Dahl; WO2015/24878; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 31804-36-1 as follows. Recommanded Product: 1-Bromo-3-methoxy-2-methylbenzene

A solution of 7g3, (9.3 g, 46 mmol), N-bromosuccinimide (8.2 g, 46 mmol) and benzoyl peroxide (450 mg, 1.8 mmol) in CCI4 (100 mL) is heated to reflux and stirred for 6 h. The reaction mixture is cooled to RT, and then filtered. The filtrate is diluted with DCM and washed successively with 2.0 N NaOH, water and brine. The organic layer is dried over MgS04, filtered and concentrated under vacuum to give 7g4.

According to the analysis of related databases, 31804-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; SIMONEAU, Bruno; DEROY, Patrick; FADER, Lee; FAUCHER, Anne-Marie; GAGNON, Alexandre; GRAND-MAITRE, Chantal; KAWAI, Steven; LANDRY, Serge; MERCIER, Jean-Francois; RANCOURT, Jean; WO2011/100838; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 31804-36-1, 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. 31804-36-1, name is 1-Bromo-3-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-bromo-l-methoxy-2-(3-methoxypropoxy)benzene (11.0 g, 54.7 mmol) in THF (120 mL) was added l-(2-thienyl)ethanone (8.97 g, 71.1 mmol), i-BuONa (7.89 g, 82.1 mmol), Pd2(dba)3 (1 g, 1.09 mmol) and Xantphos (633 mg, 1.09 mmol ) under nitrogen atmosphere. The mixture was heated at 50 C for 4 hrs, and then concentrated under reduced pressure. The residue was diluted with DCM (600 mL). The resulting organic mixture was washed with water and brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by column chromatography to afford 2-(3-methoxy-2-methyl- phenyl)-l-(2-thienyl)ethanone (13.0 g) as a brown oil.

The synthetic route of 1-Bromo-3-methoxy-2-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HAN, Xingchun; JIANG, Min; YANG, Song; (109 pag.)WO2016/128335; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 31804-36-1 as follows. category: ethers-buliding-blocks

(E)-ethyl 3-(3-methoxy-2-methylphenyl)acrylateTo a solution of 1-bromo-3-methoxy-2-methylbenzene (515 mg, 2.56 mmol) in DMF (10 ml_) at RT was added ethyl acrylate (2564 mg, 25.6 mmol) and N-ethyl-N- isopropylpropan-2-amine (2.68 ml_, 15.37 mmol), tri-o-tolylphosphine (312 mg, 1.025 mmol), Pd(OAc)2(1 15 mg, 0.512 mmol). The reaction mixture was heated in microwave under high absorption at 150 C for 2 h. The reaction mixture was passed through celite and washed with EtOAc. The filtrate was washed with water twice, brine (1x). The organic layer was collected and concentrated to give the crude product. The crude product was purified on a silica cartridge (40 g) with a Combiflash Companion, eluting at 35 mL/min with a gradient running from 0 % EtOAc/hexanes to 50 % over 35 min. The desired fractions were concentrated under reduced pressure to give 450 mg (80 %) of the title compound. LC-MS m/z 220.9 (M+H)+, 1.11 (ret. time).

According to the analysis of related databases, 31804-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem