Dimethyl Sulfide → 5-Chloro-1-benzothiophene-2-carbaldehyde

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Reaction Steps

To a mixture of N-chlorosuccinimide (13.1 mmol) and 50 ml toluene, at 0°, is slowly added dimethylsulfide (18.1 mmol). The mixture is stirred briefly, cooled to -25° and 5-chlorobenzothiophene-2-methanol (10. 1 mmol) added followed by stirring for 2 hours. Triethylamine (13.1 mmol) is added and the mixture allowed to warm to RT. The mixture is taken up in ether, washed with 10% HCl, water and brine, dried over sodium sulfate and solvent removed to give 5-chlorobenzothiophene-2-carboxaldehyde.

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