PREPARATION OF ARYL CHLORIDES FROM PHENOLS

Very few methods have been reported in the literature for converting phenols directly into arylhalides. To our knowledge, only two such processes are available to accomplish this transformation. Bestmann and Schnabel1 have found that chlorobenzene can be prepared from phenol via a phenylchloroformate intermediate produced by reaction with phosgene. This material can then be treated with triphenylphosphine, producing chlorobenzene in 67% yield by elimination of carbon dioxide. Unfortunately, triphenylphosphine remains with the product and must be deliberately removed. © 1990, American Chemical Society. All rights reserved.