1-Bromo-3-chloropropane → 4-(3-Chloropropoxy)benzamide

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Reaction Steps

A mixture of 4-hydroxybenzamide (5 g, 36.5 mmol, 1 eq), potassium carbonate (10.08 g, 72.9 mmol, 2 eq), 3-chloro-1-bromopropane (4.7 ml, 47.4 mmol, 1.3 eq) in butanone is stirred at reflux for 48 h. The solvent is then removed under vacuum and the residue is triturated in hexane and filtered. The solid is taken up in ethyl acetate and washed with a saturated solution of sodium hydrogencarbonate. The organic layer is dried over magnesium sulfate and concentrated to give 4-(3-chloropropoxy)benzamide ax54 (6.8 g) as a white solid.

Provenance & Evidence