Phthalide → 1(3H)-Isobenzofuranone, 3-bromo-

Participants

Reaction Steps

A suspension of 1.34 g of phthalide and 1.78 g of N-bromo-succinimide in 100 ml of dry carbon tetrachloride is irradiated with an ultraviolet lamp for 30 minutes. The suspension becomes clear and then a precipitation of succinimide occurs. The reaction mixture is cooled and washed with cold, dilute sodium bicarbonate and water. Concentration of the carbon tetrachloride solution affords a solid, which on recrystallization from ether-hexane affords the title compound, mp 75° - 76° C.

Provenance & Evidence