p-Xylyl bromide → (4-Methoxy-3-nitro-phenyl)-bis-(4-methyl-benzyl)-amine

Participants

Reaction Steps

To a stirred solution of 5.00 g (29.7 mmol) 4-methoxy-3-nitro-phenylamine in 60 ml acetonitrile at 0° C. were added 10.2 ml (59.5 mmol) N-ethyldiisopropylamine and 11.6 g (62.4 mmol) 4-methylbenzyl bromide. Stirring was continued at room temperature for 16 h and then the mixture was diluted with ethyl acetate and washed with 0.5 N hydrochloric acid and then with brine. The organic phase was dried over sodium sulfate and concentrated in vacuo to afford 10.4 g (93%) (4-methoxy-3-nitro-phenyl)-bis-(4-methyl-benzyl)-amine as an orange oil. ES-MS m/e (%): 399 (M+Na+, 18), 377 (M+H+, 100).

Provenance & Evidence