Boron Trichloride → 4-Methoxy-5-methyl-2-nitrophenol

A solution of 1,4-dimethoxy-2-methyl-5-nitrobenzene (6.0 g) in methylene chloride (30 mL) was cooled to −20° C., and a solution of boron trichloride (1.0 M in CH2Cl2) (30 mL) was added dropwise at −20° C. thereto. Then the reaction mixture was allowed to warm to room temperature and stirred for 16 h. To the reaction solution was then added saturated aqueous sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (100 mL×3). The combined organic layer was washed with water (100 mL), saturated brine (50 mL), dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The resulting residue was purified by column chromatography over silica gel using hexane/ethyl acetate (9:1) to give the title compound (4.25 g).

1. extractionadded saturated aqueous sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (100 mL×3)
2. washThe combined organic layer was washed with water (100 mL), saturated brine (50 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. customevaporated under reduced pressure
5. customThe resulting residue was purified by column chromatography over silica gel

ORD record

ord-70a9441c84d74c809c9f0e530b882b7a

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889727B2