Dichloromethane → 2-Bromo-5-(chloromethyl)-1,3-dimethoxybenzene

To a mixture of (4-bromo-3,5-dimethoxyphenyl)methanol (10.0 g, 40.6 mmol) and dichloromethane (100 mL) were added triethylamine (12.4 mL, 89.3 mmol) and methanesulfonyl chloride (3.46 mL, 44.7 mmol) in this order while cooling on ice, and the mixture was stirred at room temperature for 14 hours. To the mixture was added water, and then ethyl acetate was added. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=4/1) to obtain the title compound (2.47 g, 9.30 mmol).

1. temperaturewhile cooling on ice
2. stirringAfter thoroughly shaking the mixture
3. customthe organic layer was separated
4. washthe organic layer was washed with brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationThe mixture was filtered
7. distillationthe solvent in the filtrate was distilled off under reduced pressure
8. customThe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

ORD record

ord-9fdee2737a0e4f69bbfa35d7e843adc0

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530504B2