Water → 4-bromo-N-tert-butylbenzamide

Participants

Reaction Steps

Under a nitrogen atmosphere, 4.5 mL (0.043 mole) of t-butylamine was added to a solution of 7.7 grams (0.035 mole) of 4-bromobenzoyl chloride in 75 mL of tetrahydrofuran. To this was added dropwise 6.7 mL (0.048 mole) of triethylamine. Upon completion of the addition the reaction mixture was stirred at ambient temperature for about 18 hours, after which it was poured into 50 mL of water, and the organic layer was separated. The aqueous layer was extracted with one 50 mL portion of diethyl ether. The combined organic layer and extract were washed with two 25 mL portions of water, dried with sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, yielding 8.4 grams of N-t-butyl-4-bromobenzamide, mp 126-128° C. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence