Dichlorodimethylsilane → Chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane

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Under an argon atmosphere, to a solution of 10.0 g (66.6 mmol) of a mixture of 4,5-dimethyl-4H-cyclopenta[b]thiophene and 4,5-dimethyl-6H-cyclopenta[b]thiophene in 150 ml of THF, 26.6 ml of 2.5 M (66.6 mmol) nBuLi in hexanes was added dropwise over 30 min at −60° C. This mixture was additionally stirred for 2 h at room temperature and then added dropwise over 3 h to a solution of 23.7 ml (25.2 g, 200 mmol) of dichlorodimethylsilane in 50 ml of THF. The resulting mixture was stirred for 12 h at ambient temperature and then evaporated to dryness. Fractional distillation gave a yellowish liquid, bp 83-85° C./0.2 mm Hg.

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