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ChemicalBook CAS DataBase List 1-BENZOTHIOPHENE-2-SULFONYL CHLORIDE

1-BENZOTHIOPHENE-2-SULFONYL CHLORIDE synthesis

3synthesis methods
-

Yield: 53%

Reaction Conditions:

with N-chloro-succinimide;sulfur dioxide;tert.-butyl lithium in tetrahydrofuran

Steps:

34.A A.
A. Benzo[b]thiophene-2-sulfonyl chloride Benzo[b]thiophene (1.50 g, 11.2 mmol) was stirred at 0° C. in 20 ml of THF. t-Butyllithium (t-BuLi, 1.7M, 16.8 mmol, 9.9 ml) was slowly added over a 5 minute period. Fifteen minutes later, SO2 was flushed into the reaction flask and a thick white precepitate formed. The reaction mixture was stirred for 15 minutes at 0° C. and then NCS (1.64 g, 12.3 mmol) was added. The reaction was warmed to 25° C. and stirred for 30 min. It was then poured into ethyl acetate (150 ml) and washed with brine (3*100 ml). The organic phase was dried with MgSO4, filtered and concentrated to collect 2.29 g of a brown oil. The brown oil was subjected to flash chromatography (5% ethyl acetate/hexanes), which provided a yellow tan solid (1.39 g, 53% yield).

References:

Texas Biotechnology Corporation US5571821, 1996, A

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