3,4,5,6-Tetrahydrophthalic anhydride → 2-(4-Bromo-2-fluorophenyl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

A solution of 10 parts of 3,4,5,6-tetrahydrophthalic anhydride in 100 parts of glacial acetic acid was treated in one portion with 11 parts of 4-bromo-2-fluoroaniline and was stirred for 30 minutes. The reaction mixture was refluxed for 16 hours and then poured over 200 parts ice. The resulting purple crystals were filtered and recrystallized from 100 parts methanol at -40° C. to yield 13 parts of pink plates of 2-(4-bromo-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione melting at 102.0°-102.5° C.

Provenance & Evidence