Methyl iodide → 2-Methylbenzo(b)thiophene

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t-BuLi (1.7M, 26 mmoles, 15 ml) was added to a stirred solution of benzo[b]thiophene (17 mmoles, 2.3 g) and THF (30 ml) at -50° C. The resulting bright yellow reaction mixture was warmed to -30° C., and iodomethane (26 mmoles, 1.6 ml) was added. After 10 min. at -30° C., the solution was warmed to ambient temperature and stirred an additional 30 min., then diluted with ether (100 ml) and washed with brine (2×100 ml). The organic phase was dried (MgSO4), filtered and concentrated to collect 2.48 g (98%) of 2-methylbenzo[b]thiophene as a light yellow solid.

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