Ethyl Bromide → 2-Ethoxy-1H-isoindole-1,3(2H)-dione

Participants

Reaction Conditions

Reaction Steps

A solution of 24 g (0.147 moles) of N-hydroxyphthalimide in 120 ml of dimethyl sulfoxide is warmed at 40° up to complete dissolution. Then 23.9 g (0.176 moles) of sodium acetate trihydrate and 15.92 ml (0.21 moles) of ethyl bromide are added, while warming at 80° C. After two hours and 15 minutes, the mixture is diluted with 600 ml of chloroform, washed with 10% potassium bicarbonate and dried. Removal of the solvent leaves 19.3 g (68.7%) of N-ethoxy-phthalimide, melting point 95°-97° C. (A. Rougny et al, Bull. Soc. Chim. Fr. 1976, pp. 833).

Provenance & Evidence