Methanol → (3-Bromo-5-fluorophenyl)methanol

Temperature

0 °C

3-Bromo-5-fluorobenzoic acid (1.0 g, 4.52 mmol) was suspended in tetrahydrofuran (8 mL) and cooled to 0° C. To this solution was added borane tetrahydrofuran complex (1 M in tetrahydrofuran, 9 mL, 9.0 mmol) cautiously over 15 min. The reaction mixture was allowed to warm to room temperature overnight. The mixture was cooled to 0° C., treated with excess methanol, diluted with ethyl acetate, washed with 1 N sodium hydroxide (2×), then brine (2×), dried over sodium sulfate, and concentrated to afford 0.88 g (95%) as a white powder. 1H-NMR (CDCl3, 500 MHz) 7.29 (s, 1H), 7.16 (d, J=7.9 Hz, 1H), 7.03 (d, J=9.2 Hz, 1H), 4.66 (s, 2H).

1. temperatureto warm to room temperature overnight
2. temperatureThe mixture was cooled to 0° C.
3. washwashed with 1 N sodium hydroxide (2×)
4. dry with materialbrine (2×), dried over sodium sulfate
5. concentrationconcentrated
6. customto afford 0.88 g (95%) as a white powder

ORD record

ord-1ce982a56fdd4bfd8710c0853567e76c

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08383821B2