Water → 7-Chlorothieno[3,2-b]pyridine

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Reaction Steps

To a solution of DMF (13.2 mL, 170 mmol) in DCM (100 mL) at 0° C. was added oxalyl chloride (22 mL, 252 mmol) in DCM (100 mL) very slowly over 1 hour. To the resulting white gel solution was added the 3H-thieno[3,2-d]pyrimidin-4-one (12 g, 79 mmol). The mixture was refluxed for 4 hours. After cooling, the mixture was purred into water (500 mL) and extracted with DCM (3×250 mL). Then the organic phase was dried over magnesium sulfate, filtered and concentrated to afford 7-chloro-thieno[3,2-b]pyridine as white solid (13.4 g, 99%). 1H NMR (CDCl3, 400 Hz) δ 9.00 (s, 1H), 8.06 (d, J=5.6 Hz, 1H), 7.61 (d, J=5.6 Hz, 1H). MS (ESI+) [M+H]+ 170

Provenance & Evidence