Water → 5-bromo-3-hydroxy-3H-isobenzofuran-1-one

Participants

Reaction Steps

A mixture of 13.3 gm 5-bromophthalide and 12.7 gm N-bromosuccinimide in 480 ml carbon tetrachloride was irradiated with a tungsten floor lamp and refluxed for 3 hours. The reaction was followed by NMR. The succinimide was filtered off and the cake washed with carbon tetrachloride. The solvent was removed in vacuo leaving a residue of 19.2 gm, to which was added 100 ml water. This mixture was refluxed with stirring for 4 hours, then the mixture was cooled and the product filtered off, washed neutral with water and dried. Wt=9.9 gm.

Provenance & Evidence