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 the mixture was stirred at 50° C. for 2 h (monitored by TLC). The reaction was quenched by adding HCl (20 mL, 3 N) after which the result mixture was stirred for 2 h and then 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). Then 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, 2H), 7.19-7.22 (m, 1H), 7.47 (t, J=8.8 Hz, 1 H), 7.73-7.77 (m, 1H); 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) after which the result mixture
3. customTHF was removed under vacuum
4. extractionThe aqueous layer was extracted with AcOEt (30 mL)
5. extractionThen the 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-f20cc11fa83a402f8eb76aba3defb017

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071588B2