4-Aminophenol → 3,4-dichloro-N-(4-hydroxyphenyl)benzamide

Participants

Reaction Steps

4-Aminophenol (1.9 g, 17 mmol) was diluted with DMF (40 mL) followed by the addition of pyridine (0.978) (1.4 mL, 17 mmol) and 3,4-dichlorobenzoyl chloride (3.0 g, 14 mmol) in 5 mL of DMF. After stirring for 12 hours, the reaction mixture was diluted with ethyl acetate and 2N HCl. The aqueous layer was extracted once with ethyl acetate. The organics were combined, washed with water, brine, dried over MgSO4, filtered and concentrated onto silica gel. The material was purified using a biotage 40M column eluting with hexanes:ethyl acetate (9:1) using 2 L and then (60:40) 1 L to yield 3,4-dichloro-N-(4-hydroxyphenyl)-benzamide (1.5 g, 37% yield) as a white solid.

Provenance & Evidence