Dimethylformamide → 4-Bromo-2-chloro-N,N-dimethylaniline

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Reaction Steps

Under nitrogen, 11.6 mL (186 mmol) of iodomethane was added to a stirred solution of 12.8 g (62 mmol) of 4-bromo-2-chloroaniline and 42.8 g (310 mmol) of powdered K2CO3 in 200 mL of DMF. Purification by silica gel chromatography (Waters Prep-500A)with ethyl acetate/hexane (5:95) gave 11.3 g (78%) of 4-bromo-2-chloro-N,N-dimethylaniline as a colorless liquid: NMR (CDCl3) δ 2.79 (s, 6H), 6.92(d, J=9 Hz, 1H), 7.25-7.34 (m, 1H), 7.49 (d, J=2 Hz, 1H).

Provenance & Evidence