Bromine → 2-(Benzyloxy)-5-(2-oxiranyl)benzamide

Participants

Reaction Steps

5-Acetyl-2-(phenylmethoxy)benzamide (10.0 g, 37.1 mmol) was dissolved in chloroform and brought to reflux. Bromine (1.98 g, 12.4 mmol) was added. The solution was allowed to cool to room temperature. After 10 minutes the bromine color had disappeared and a second portion of bromine was added. A third portion of bromine was added after the color had again discharged and the solution refluxed for a further 10 minutes. The flask was allowed to cool and placed in the freezer overnight. The solvent was removed in vacuo and the residue crystallized from ethanol to provide the title compound (11.3 g, 32.4 mmol).

Provenance & Evidence