Boron trifluoride → (2-Fluoro-5-methoxy-4-nitrophenyl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of 2-fluoro-5-methoxy-4-nitrobenzoic acid (Compound 130E, 1.60 g, 7.44 mmol) in THF (23.6 mL) is slowly charged with sodium borohydride (0.633 g, 16.8 mmol) and stirred for 5 minutes. A solution of boron trifluoride, ethyl ether complex (0.895 mL, 7.26 mmol) in THF (7.85 mL) is added to the reaction mixture. The resulting solution is heated at reflux for 4 h. The reaction mixture was cooled to 0° C., then quenched with ice (15 mL) and diluted with ether (25 mL) and 2 N NaOH (10 mL). The ether layer was washed with brine (15 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield an off-white solid, 1.45 g (97% yield). This material was used without any further purification. 1H NMR (CDCl3, 400 MHz): δ=3.99 (s, 3 H), 4.86 (s, 2 H), 7.29 (d, J=5.81 Hz, 1 H), 7.64 (d, J=9.09 Hz, 1 H). MS (ES+): m/z 202.05 [MH+] (TOF, polar).

Provenance & Evidence