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 that order while cooling on ice, and the mixture was stirred at room temperature for 14 hours. Water was added to the mixture, 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 (mixture 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 (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=4/1)

ORD record

ord-27fa93894c204e5092bc667ea1f8544b

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08431603B2