Ammonia → 1-(4-Bromo-2-fluorophenyl)ethan-1-amine

To a solution of 1-(4-bromo-2-fluorophenyl)ethanone (2.0 g, 9.2 mmol) in methanol (50 mL) was added ammonia (7 N in methanol, 8.0 mL, 55 mmol) and titanium(IV) isopropoxide (5.4 mL, 18 mmol). The reaction mixture was stirred at room temperature for 18 h, cooled to 0° C. and sodium borohydride (520 mg, 14 mmol) was added. The reaction mixture was warmed to room temperature, stirred for 20 min, quenched with 2 M ammonium hydroxide and filtered. The reaction mixture was extracted with methylene chloride and the combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford the desired product (1.2 g, 63%) as an oil: ESI MS m/z 219 [C8H9BrFN+H]+.

1. temperaturecooled to 0° C.
2. temperatureThe reaction mixture was warmed to room temperature
3. stirringstirred for 20 min
4. customquenched with 2 M ammonium hydroxide
5. filtrationfiltered
6. extractionThe reaction mixture was extracted with methylene chloride
7. dry with materialthe combined organic layers were dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-e98eb4c1e44b4e0a94bb08d3bfb9eb2f

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962648B2