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ChemicalBook CAS DataBase List 2-BROMO-5-METHYL-4-NITROANISOLE
861076-28-0

2-BROMO-5-METHYL-4-NITROANISOLE synthesis

9synthesis methods
-

Yield: 87.8%

Reaction Conditions:

Stage #1:methanol with sodium at 0; for 0.5 h;
Stage #2:3-bromo-4-fluoro-6-methylnitrobenzene at 30; for 2 h;

Steps:

28
1-Bromo-2-methoxy-4-methyl-5-nitrobenzene Na (351 mg, 15.28 mmol) was added into CH3OH (20 mL) and the resulting mixture was stirred at 0 °C for 30 min. 1-Bromo-2-fluoro-4-methyl-5- nitrobenzene (3.25 g, 13.89 mmol) was added to the mixture and then stirred at 30 °C for 2 h. The solvent was removed and the residue was dissolved in H2O, extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether = 1:50) to yield the product as a white solid (3.0 g, 87.8% yield).

References:

ARAXES PHARMA LLC;LI, Liansheng;FENG, Jun;WU, Tao;REN, Pingda;LIU, Yi;LIU, Yuan;LONG, Yun, Oliver WO2015/54572, 2015, A1 Location in patent:Page/Page column 247

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