Triethylamine → 2-Bromo-1,3-dimethoxy-5-(methoxymethyl)benzene

Participants

Reaction Steps

Under cooling in an ice water bath, to a solution of (4-bromo-3,5-dimethoxyphenyl)methanol (100 g, 405 mmol) and triethylamine (67.5 mL, 484 mmol) in dimethoxyethane (1000 mL) was added mesyl chloride (34.5 mL, 446 mmol), and the reaction mixture was further stirred for 30 minutes. Then, to the reaction mixture was added a 28% sodium methoxide methanol solution (350 mL, 1.72 mol), and the reaction mixture was stirred at room temperature for 3 hours. After the reaction, toluene (1000 mL) and water (1000 mL) were added to the reaction mixture, then, an aqueous layer was removed, and an organic layer was washed sequentially with water (1000 mL), 1N hydrochloric acid (500 mL) and water (500 mL), then, the solvent was concentrated under reduced pressure, to obtain 105 g of a title compound as colorless oil (yield: 99.5%).

Provenance & Evidence