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

Temperature

0 °C

3-Bromo-5-nitrobenzoic acid (3.2 g, 13.0 mmol) was suspended in tetrahydrofuran (25 mL) and cooled to 0° C. To this solution was added borane tetrahydrofuran complex (1 M in tetrahydrofuran, 26 mL, 26 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 3.0 g (99%) as a white powder. 1H-NMR (CDCl3, 300 MHz) 8.24 (s, 1H), 8.13 (s, 1H), 7.82 (s, 1H), 4.78 (s, 2H). Mass spec.: 233.88 (MH)+.

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 3.0 g (99%) as a white powder

ORD record

ord-1ab653f2233a42e5b073c8f28583978c

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08383821B2