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

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%).

1. stirringthe reaction mixture was stirred at room temperature for 3 hours
2. additionwere added to the reaction mixture
3. customan aqueous layer was removed
4. washan organic layer was washed sequentially with water (1000 mL), 1N hydrochloric acid (500 mL) and water (500 mL)
5. concentrationthe solvent was concentrated under reduced pressure

ORD record

ord-8958fba62f0340dab67556691ded2155

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858809B2