Propanoyl bromide, 2-bromo- → 2-Bromo-N-(4-butoxy-2,6-dimethylphenyl)propanamide

Participants

Reaction Steps

To a chilled (ca 10°) solution of 50.7 g (0.263 mole) of 4-butoxy-2,6-dimethylaniline [Buchi et al., Helv. Chim. Acta, 34, 278 (1951)] in 224 ml glacial acetic acid was added rapidly 62.4 g (.289 mole) of 2-bromo-propionyl bromide and immediately thereafter a chilled (ca 5°) solution of 87.2 g sodium acetate trihydrate in 362 ml water. This mixture was shaken for 1/2 hour, filtered, washed with water until the washes were neutral, and dried in vacuo over silica gel and KOH; yield 68.9 g (71.6%); m.p. 132.5°-133.5°. The product was recrystallized from 95% ethanol; m.p. 135.5°-136°.

Provenance & Evidence