Methanol → (2-Bromo-6-nitrophenyl)methanamine

A mixture of 1-bromo-2-fluoro-3-nitrobenzene (3.96 g, 18 mmol), 2M methylamine in MeOH (18 mL, 36 mmol) and DIPEA (3.3 mL, 19 mmol) was stirred for 3 h at RT. The reaction mixture was concentrated in vacuo. The resulting residue was taken up in DCM (100 mL) and washed with sat. NaHCO3 (100 mL). The aqueous layer was further extracted with DCM (100 mL). The combined organic fractions were washed with brine (50 mL), dried over Na2SO4 and concentrated in vacuo to afford the title compound as bright orange oil (4.16 g, 99%). LCMS (Method C): RT 3.39 min [M+H]+ 231 (for 79Br). 1H NMR (CDCl3, 400 MHz): δ 7.86 (1H, dd, J=8.5, 1.5 Hz), 7.67 (1H, dd, J=8.0, 1.5 Hz), 6.67 (1H, dd, J=8.5, 8.0 Hz), 3.13 (1H, bs), 3.01 (3H, d, J=5.5 Hz).

1. concentrationThe reaction mixture was concentrated in vacuo
2. washwashed with sat. NaHCO3 (100 mL)
3. extractionThe aqueous layer was further extracted with DCM (100 mL)
4. washThe combined organic fractions were washed with brine (50 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo

ORD record

ord-e4a4c477117644e1ad708fd71fbf926d

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653089B2