Sodium Carbonate → HCID 11609103, compound

Participants

Reaction Conditions

Reaction Steps

Zinc dust (16 g) was added in portions over 2 hours to N-(4-bromo-2-methyl-6-nitro-phenyl)-3,3-dimethyl-butyramide (2.74 g) in tetrahydrofuran (50 mL) and acetic acid (12 mL) cooled to 0° C., and then stirred 30 minutes at 25° C. The reaction mixture was poured into a suspension of sodium carbonate (16 g) in tetrahydrofuran and filtered through silica (50 g), which was washed with ethyl acetate (100 mL). The organic phase was concentrated in vacuo to furnish 2.47 g (100% yield) of the title compound as a pale red solid. LC-MS (m/z) 300 (MH+); tR=2.54, (UV, ELSD) 96%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.04 (s, 9H), 2.05 (s, 3H), 2.21 (s, 2H), 4.94 (s, 2H), 6.59 (d, 1H), 6.74 (d, 1H), 8.85 (s, 1H).

Provenance & Evidence