3,5-Difluorobenzonitrile → 3-Fluoro-5-methoxybenzonitrile

Sodium methoxide (1.50 ml of a 4.5M solution in methanol, 7.10 mmol) was added dropwise to a stirred solution of 3,5-difluorobenzonitrile (1.00 g, 7.10 mmol) in N,N-dimethylformamide (36 ml) at 0° C. under nitrogen. The reaction was allowed to warm to room temperature and stirred for 14 hours. The reaction was diluted with ether (40 ml), washed with water (3×100 ml) and brine (100 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with cyclohexane:ethyl acetate (95:5, by volume) to provide the title compound (418 mg) as a yellow oil.

1. washwashed with water (3×100 ml) and brine (100 ml)
2. dry with materialdried over magnesium sulphate
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customThe crude product was purified by flash chromatography on silica gel eluting with cyclohexane:ethyl acetate (95:5, by volume)

ORD record

ord-1b85e8bf4a6c4b7b8e46628a8cabf164

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07109228B2