Hexahydrophthalic anhydride → 2-(4-Bromo-2-fluorophenyl)hexahydro-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

11.4 Parts of 4-bromo-2-fluoroaniline were added to a solution of 10 parts of cyclohexane-1,2-dicarboxylic anhydride in 100 parts of glacial acetic acid and the mixture was stirred for 2 hours. The mixture was refluxed for 20 hours and then poured onto 200 parts of ice. The resulting purple crystals were filtered and recrystallized from 70 parts of methanol at -40° to yield 7.6 parts of lavender crystals of 2-(4-bromo-2-fluorophenyl)-3a,4,5,6,7,7a-hexahydro-1H-isoindole-1,3(2H)-dione melting at 90°-92°.

Provenance & Evidence