Dimethyl Sulfide → (3-Bromo-2-fluorophenyl)methanamine

To a solution of 3-bromo-2-fluorobenzamide (3.0 g, 13.76 mmol) in THF (50 mL) was added BH3.Me2S (1.57 mL, 20.6 mmol) and stirred at 50° C. for 2 h (monitored by TLC). The reaction was quenched by adding HCl (20 mL, 3 N) and the result mixture was stirred for 2 h before THF was removed under vacuum. The aqueous layer was extracted with AcOEt (30 mL), and then was adjusted to pH=9.0 with NaOH (1 N). The aqueous layer was extracted with AcOEt (50 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give 1.30 g of the title compound, as a colorless oil (yield: 46%). 1H NMR (400 MHz, D2O): δ 4.30 (S, 2 H), 7.19-7.22 (m, 1 H), 7.47 (t, J=8.8 Hz, 1 H), 7.73-7.77 (m, 1 H); 13C NMR (100 MHz, D2O): δ 37.4, 108.9, 121.2, 126.2, 130.7, 135.1, 156.2, 158.6.

1. customThe reaction was quenched
2. additionby adding HCl (20 mL, 3 N)
3. customwas removed under vacuum
4. extractionThe aqueous layer was extracted with AcOEt (30 mL)
5. extractionThe aqueous layer was extracted with AcOEt (50 mL×2)
6. washThe combined organic layers were washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-8a420ac046aa49be843f7bcb0af779ba

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08067408B2