Ammonia → HCID 67403497, compound

To a mixture of 1-(4-bromo-2,6-difluorophenyl)ethanone (450 mg, 0.91 mmol), titanium isopropoxide (1.14 mL, 4.61 mmol) in ethanol (10 mL) was added a solution of 2M ammonia in ethanol (4.8 mL, 9.6 mmol), and the resulting mixture was stirred at room temperature. After 18 hours, sodium borohydride (115 mg, 3.48 mmol) was added and stirring was continued at room temperature for three hours. The reaction mixture was poured into a 2M aqueous ammonium hydroxide solution (100 mL) then filtered. The filtrate was extracted with ethyl acetate (3×50 mL), and the combined extract was washed with water (100 mL), then brine (100 mL), dried over sodium sulfate, filtered and concentrated to give 1-(4-bromo-2,6-difluorophenyl)ethanamine (236 mg, 62% yield), MS (EI) for C8H8BrF2N: 237 (MH+).

1. stirringstirring
2. waitwas continued at room temperature for three hours
3. filtrationthen filtered
4. extractionThe filtrate was extracted with ethyl acetate (3×50 mL)
5. extractionthe combined extract
6. washwas washed with water (100 mL)
7. dry with materialbrine (100 mL), dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-a0689e8a61634b04b0fd15c5211b0bbe

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08012956B2