Water → 5-(2,4-Dichlorophenylsulfanyl)-4-nitrothiophene-2-carbaldehyde

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Reaction Steps

To suspension of potassium t-butyloxide (0.412 g, 3.67 mmol) in anhydrous tetrahydrofuran (20 mL), 2,4-dichlorobenzenethiol (0.6 g, 3.34 mmol) was added. The resulting mixture was stirred at ambient temperature for 15 minutes. After this time, a solution of 5-chloro-4-nitrothiophene-2-carbaldehyde (0.64 g, 3.34 mmol) in anhydrous tetrahydrofuran (5 mL) was added and the reaction mixture was stirred at ambient temperature for 2 hours. Then the above mixture was further heated under reflux for 2 hours. After this time, the reaction was cooled to ambient temperature and was poured into water (150 mL). The product was extracted into dichloromethane (3×100 mL). The organic layer was separated, washed with saturated brine (2×250 mL) and dried (MgSO4). The solvent was removed under reduced pressure to give a sticky orange solid. The crude solid was purified by silica gel chromatography using an 80:20 mixture of hexane and ethyl acetate as eluent. The fractions containing the product were combined and the solvents removed in vacuo. The residual yellow solid was triturated with a small amount of hexane, collected by filtration and dried in vacuo to afford the title compound as a yellow solid (0.92 g, 82% yield). 1H NMR (300 MHz, CDCl3) δ: 9.70 (1H, s), 8.19 (1H, s), 7.70 (1H, d, J=8.37 Hz), 7.68 (1H, d, J=2.21 Hz), 7.44 (1H, dd, J=8.37, 2.21 Hz).

Provenance & Evidence