p-Chlorothiophenol → 5-[(4-Chlorophenyl)sulfanyl]-2-thiophenecarbaldehyde

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Reaction Steps

Sodium hydride (60%, 1.2 g, 30 mmol) is added to a solution of 4-chlorothiophenol (4.3 g, 30 mmol) in THF (30 mL). The resulting solution is stirred for 10 minutes then the solvent is removed in vacuo. Acetone (60 mL) is added followed by 5-bromothiophene-2-carboxaldehyde (3.0 mL, 25 mmol). The mixture is stirred at rt for 2 h. The solvent is removed in vacuo and the resulting slurry diluted with CH2Cl2. This solution is washed three times with 1N NaOH then dried over MgSO4, filtered and concentrated in vacuo. The crude product is purified by flash column chromatography (gradient of 1 to 5% EtOAc in heptane) to give 6.2 g (98%) of 5-(4-chlorophenylsulfanyl)thiophene-2-carboxaldehyde. 1H NMR (300 MHz, CDCl3)δ7.13, 7.31-7.39, 7.63, 9.78.

Provenance & Evidence