2-Aminophenol → 4-bromo-N-(2-hydroxyphenyl)benzamide

Participants

Reaction Conditions

Reaction Steps

In a 200 mL three-neck flask, 2.2 g (20 mmol) of 2-aminophenol, 3.0 mL (22 mmol) of triethylamine, and 50 mL of tetrahydrofuran (THF) were placed. Then, the mixture was cooled to 0° C. After cooling, 50 mL of a THF solution containing 4.5 g (20 mmol) of 4-bromobenzoyl chloride was dripped under nitrogen stream. This solution was stirred at 0° C. for 4 hours under nitrogen stream. After a certain period, the solution was added to water, and an aqueous layer was extracted with ethyl acetate. The resulting extracted solution and the organic layer were combined and washed with 0.2 M hydrochloric acid and a saturated aqueous solution of sodium hydrogen carbonate, and then the organic layer was dried with magnesium sulfate. The mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and the filtrate was condensed to give a solid. The solid was recrystallized with ethyl acetate/hexane, so that 5.3 g of target white powder was obtained in a yield of 88%.

Provenance & Evidence