Hydrochloric Acid → 3-Chloro-4-fluorobenzoic acid

Reaction equation

C[C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([Cl:11])[CH:5]=1)=[O:3].Br[O-].[Na+].S([O-])(O)=[O:16].[Na+].Cl>>[Cl:11][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[F:10])[C:2]([OH:3])=[O:16]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 5204223'-Chloro-4'-fluoroacetophenone

HCID 23665763Sodium Bisulfite

HCID 23673712Sodium hypobromite

Product 1

HCID 5209893-Chloro-4-fluorobenzoic acidYield 74%

Procedure

The 3-chloro-4-fluoroacetophenone is then reacted with an aqueous solution of sodium hypobromite, the aqeuous phase is treated with sodium hydrogensulfite and acidified with hydrochloric acid, and the precipitated product is recrystallized from benzene. 3-Chloro-4-fluorobenzoic acid obtained in a yield of 74%.