[N+:1]([C:4]1[CH:5]=[C:6]([SH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[OH-].[K+].[Cl:13][C:14]([F:18])=[C:15]([F:17])[F:16].ClC1C(C(F)(F)CF)=CC=CC=1[N+]([O-])=S>[Hg].CC(C)=O>[Cl:13][CH:14]([F:18])[C:15]([F:17])([F:16])[S:10][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][CH:7]=1
A mixture of 50 g. (0.322 moles) of 3-nitrothiophenol, 46.6 g. (0.402 moles) of potassium hydroxide, 60 ml. of acetone and 59 g. (0.395 moles) of 2-chloro-1,1,2-trifluoroethylene is heated in an autoclave with stirring for 11/2 hours at 60°-70° C. The reaction mixture is cooled, decanted and the solution evaporated to dryness in vacuo. The oily residue is combined with the solids, water is added and the product extracted with methylene chloride. The extracts are washed with 2.5 N aqueous sodium hydroxide and water, dried and evaporated to dryness in vacuo affording 76.5 g. of 3(2-chloro 1,1,2-trifluoroethylthio nitrobenzene with a b.p. at 0.25 mm. of mercury of 98°-102° C. The structure is verified with nuclear magnetic resonance.
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