Water → Benzaldehyde, p-phenylthio-

Participants

Reaction Steps

Benzenethiol (500 mg, 4.54 mmol) was dissolved in 6 mL of DMF. K2CO3 (940 mg, 6.81 mmol) was added and the resulting mixture was stirred at room temperature for 10 mins. 4-Fluoro-benzaldehyde (675 mg, 5.44 mmol) was then added and the resulting mixture was stirred at 50° C. for 2 hours. The mixture was then stirred at 80° C. for 3 hours. Water was added and the product was extracted with EtOAc and washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford crude product. Purification by column chromatography (using silica gel of mesh size of 60-120 and 5/95 EtOAc:hexane as the eluent) afforded 940 mg (96% yield) of 4-phenylsulfanyl-benzaldehyde. LC-MS purity: 91.3%

Provenance & Evidence