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

Mesyl chloride (34.5 mL, 446 mmol) was added to a solution of (4-bromo-3,5-dimethoxyphenyl)methanol (100 g, 405 mmol) and triethylamine (67.5 mL, 484 mmol) in 1.2-dimethoxyethane (1000 mL) while cooling with ice, and the reaction mixture was stirred for 30 minutes. After adding a 28% sodium methoxide in methanol (350 mL, 1.72 mol) to the reaction mixture, it was further stirred for 3 hours at room temperature. Upon completion of the reaction, toluene (1000 mL) and water (1000 mL) were added to the reaction mixture, the aqueous layer was removed, and the organic extract was washed with water (1000 mL), 1N hydrochloric acid (500 mL) and water (500 mL) in that order and concentrated under reduced pressure to afford 105 g of the title compound as a colorless oil (99.5% yield).

1. temperaturewhile cooling with ice
2. stirringwas further stirred for 3 hours at room temperature
3. additionwere added to the reaction mixture
4. customthe aqueous layer was removed
5. extractionthe organic extract
6. washwas washed with water (1000 mL), 1N hydrochloric acid (500 mL) and water (500 mL) in that order
7. concentrationconcentrated under reduced pressure

ORD record

ord-010d34d98dd24f95b563cc8a7cdee595

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07176216B2