4'-Mercaptoacetophenone ethylene acetal → 1-(4-Sulfanylphenyl)ethan-1-one
Reaction equation
C1O[C:4]([C:6]2[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=2)([CH3:5])[O:3]C1>C(O)CO>[SH:12][C:9]1[CH:10]=[CH:11][C:6]([C:4](=[O:3])[CH3:5])=[CH:7][CH:8]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
4'-Mercaptoacetophenone ethylene acetal (0.656 g; obtained by the reaction of 4'-mercaptoacetophenone and ethylene glycol using an analogous procedure to that described in the third paragraph of the portion of Example 7 which is concerned with the preparation of starting materials) was added to a mixture of 2,4-dibromothiazole (0.82 g), potassium carbonate (0.468 g) and NMP (4 ml). The mixture was stirred and heated to 90° C. for 2.5 hours. The mixture was cooled to ambient temperature and partitioned between diethyl ether and brine. The organic phase was dried (MgSO4) and evaporated. The mixture was purified by column chromatography using a 3:1 mixture of ethyl acetate and petroleum ether as eluent. There was thus obtained 4'-[4-bromothiazol-2-ylthio]acetophenone ethylene acetal (1.1 g, 90%), m.p. 71° C.