Water → 1-Bromo-3-cyclopropylthiobenzene
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[CH3:1][C:2]([CH3:5])([O-])C.[K+].C1(Br)CC1.[Br:11][C:12]1[CH:13]=[C:14]([SH:18])[CH:15]=[CH:16][CH:17]=1.O>CS(C)=O>[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH:5]2[CH2:2][CH2:1]2)[CH:13]=1[CH3:1][C:2]([CH3:5])([O-])C.[K+].C1(Br)CC1.[Br:11][C:12]1[CH:13]=[C:14]([SH:18])[CH:15]=[CH:16][CH:17]=1.O>CS(C)=O>[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH:5]2[CH2:2][CH2:1]2)[CH:13]=1Potassium t-butoxide (4 g) and cyclopropyl bromide (7.6 mL) were added to a solution of 3-bromothiophenol (6 g) in dimethyl sulfoxide (30 mL), and the mixture was stirred at 80° C. for five hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and brine, dried over sodium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→7:3) to give the title compound as a light yellow oil (1.6 g, 23%).
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