Water → 3-Fluoro-4-nitroanisole

A mixture of 3-fluoro-4-nitrophenol (2.56 g), potassium carbonate (4.5 g) and iodomethane (4.63 g) in N,N-dimethyl-formamide (15 mL) was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was washed with diethyl ether. The extract was washed with water twice, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 3-fluoro-4-nitroanisole (2.56 g). This material was dissolved in 1,2-dichloroethane (13 mL). To the solution was added chlorosulfonic acid (1.3 mL), and the mixture was heated for reflux for 4 hours. The reaction mixture was diluted with methylene chloride, and the resulting mixture was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1) to give the title compound (0.51 g).

1. washthe resulting mixture was washed with diethyl ether
2. washThe extract was washed with water twice
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe solvent was removed under reduced pressure

ORD record

ord-74af3b76bbd34d98ba9e39132236ca73

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040693B2