Water → 2-(4-Bromo-3,4,4-trifluorobutylthio)-5-chlorothiazole

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Reaction Steps

The compound from Step 1 (30.6 g) in dichloromethane (130 cm3) was treated at ambient temperature with sulfuryl chloride (9.6 cm3) in dichloromethane (30 cm3) over 1 hour with stirring under an atmosphere of nitrogen. The reaction was stirred for a further 1 hour, poured slowly into water (250 cm3) and stirred for 0.25 hours. The organic phase was separated, the aqueous phase extracted with dichloromethane (2×75 cm3), the combined organic phases washed with aqueous sodium hydrogen carbonate, brine and dried (MgSO4). The solvent was evaporated under reduced pressure and the residue fractionated by chromatography (silica; eluant 5% diethyl ether in hexane) to give 2-(4-bromo-3,4,4-trifluorobutylthio)-5-chlorothiazole (28.0 g); 1H NMR: δ 2.20-2.45 (2H,m); 3.25-3.50(2H,m); 4.70-5.0(1H,m); 7.45(1H,s); (oil).

Provenance & Evidence