4-Bromo-2,6-difluorobenzonitrile → 4-Bromo-2-fluoro-6-methoxybenzonitrile

To a solution of 4-bromo-2,6-difluorobenzonitrile (1, 15.0 g, 69 mmol) in THF (100 mL) at 0° C. was slowly added sodium methoxide (25% wt in methanol, 14.9 g, 69 mmol) and the mixture was stirred at room temperature for 16 h. The mixture was concentrated and partitioned between dichloromethane (500 mL) and water (250 mL). The organic extracts were dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel chromatography eluting with ethyl acetate in hexane (0-100%) to afford the title compound (15.2 g, 99%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 7.01-6.99 (m, 1H), 6.94 (s, 1H), 3.96 (s, 1H).

1. customat 0° C.
2. concentrationThe mixture was concentrated
3. custompartitioned between dichloromethane (500 mL) and water (250 mL)
4. dry with materialThe organic extracts were dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by silica gel chromatography
8. washeluting with ethyl acetate in hexane (0-100%)

ORD record

ord-f6637e0155f24b228262c086adfe4b91

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278940B2