4-Bromodiphenyl Ether → 4-Phenoxythiophenol
Reaction equation
C[S-:2].[Na+].[CH:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>CN(C)C=O>[O:10]([C:11]1[CH:16]=[CH:15][C:14]([SH:2])=[CH:13][CH:12]=1)[C:7]1[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of sodium thiomethoxide (25 g) and 4-bromodiphenyl ether (25 g) in N,N-dimethylformamide (DMF) (150 ml) was refluxed overnight. The mixture was cooled and added to dilute aqueous sodium hydroxide. The water layer was washed with ether to remove by-products and acidified with hydrochloric acid. The product, 4-(phenoxy)thiophenol, was extracted with ether, and the ether layer dried and evaporated to give 4-(phenoxy)thiophenol (19-20 g) as a red oil. This material can be used without further purification.