Phenyl phosphorus dichloride → 3-Chlorophthalic anhydride

Participants

Reaction Conditions

Reaction Steps

Chlorine gas (363 milligrams, 5.18 millimoles) was bubbled into a solution of dichlorophenylphosphine (927 milligrams, 5.18 millimoles) in dichlorophenylphosphine oxide (10 milliliters). To this yellow solution was added 3-nitrophthalic anhydride (1 gram, 5.18 millimoles), then the reaction mixture was heated to 150° C. for 12 hours. The cooled solution was poured onto ice (20 milliliters) and neutralized with 50% aqueous sodium hydroxide. The aqueous mixture was extracted twice with 20 milliliter portions of ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate and concentrated in vacuo to yield 3-chlorophthalic anhydride (780 milligrams, 83 weight percent) as a dark solid.

Provenance & Evidence