4-Isopropylaniline → 2-Bromo-2-methyl-N-[4-(propan-2-yl)phenyl]pentanamide

Participants

Reaction Steps

410 mg (3.04 mmoles) of 4-isopropylaniline was dissolved in 10 ml of benzene, and 500 mg of triethylamine was added. With stirring under ice cooling, 800 mg (4.10 mmoles) of 2-bromo-2-methylvaleryl chloride was added dropwise. After the addition, the mixture was further stirred at room temperature for 1 hour. The crystals that precipitated were separated by filtration. The filtrate was concentrated, and the residue was recrystallized from benzene to give 620 mg of 2-bromo-2-methyl-4'-isopropylvaleranilide. m.p. 87.2°-88.2° C. IR νmaxcm-1 3300 and 1650. Yield 65.4%.

Provenance & Evidence