Hydrochloric Acid → 1,4-Benzenediamine, 2-bromo-6-(trifluoromethyl)-

Aqueous hydrochloric acid (2 M, 45 mL) was added slowly to a mixture of zinc dust (8.6 g) and 2-bromo-4-nitro-6-trifluoromethyl-phenylamine (2.5 g) in tetrahydrofuran (50 mL). The reaction mixture was stirred for 1 hour, filtered and neutralized with saturated aqueous sodium bicarbonate (100 mL). Water (100 mL) was added and the mixture was extracted with ethyl acetate (2×100 mL). The combined organic phases were washed with water (2×200 mL) and brine (200 mL), dried over sodium sulfate and concentrated in vacuo to furnish 2.22 g (98% yield) of the title compound as a red solid. 1H NMR (500 MHz, DMSO-d6): 4.55 (s, 2H), 4.91 (s, 2H), 6.76 (d, 1H), 7.01 (d, 1H).

1. filtrationfiltered
2. additionWater (100 mL) was added
3. extractionthe mixture was extracted with ethyl acetate (2×100 mL)
4. washThe combined organic phases were washed with water (2×200 mL) and brine (200 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo

ORD record

ord-0407e683b78f4bf7b22250c0ba3dcd5d

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299075B2