Chloroform → 4-[(5-Bromopentyl)sulfanyl]-7-(trifluoromethyl)quinoline

Participants

Reaction Conditions

Reaction Steps

7-Trifluoromethyl-4-quinoline-thiol (5 g, 21.8 mmol), 1,5-dibromopentane (23.7 g, 98.1 mmol) and CHCl3 (60 mL) were charged in a 250 ml round-bottomed flask equipped with a magnetic stirrer. TBABr (0.7 g, 2.2 mmol) and water (40 mL) were added and the reaction mixture was stirred for 48 h at 20° C. The reaction mixture was poured in 100 mL of H2O with K2CO3 (3.0 g, 21.8 mmol) and extracted with CH2Cl2 (400 mL). The organic layer was washed with water (30 mL), brine (2×30 mL), dried over MgSO4, filtered and evaporated at 30° C. to dryness. The crude compound was purified by column chromatography (SiO2:CH2Cl2:MeOH=99.5:0.5 to 98:2) to give after evaporation 4-(5-bromopentylthio)-7-(trifluoromethyl)quinoline 25 (5.9 g, 72% yield) as a white solid.

Provenance & Evidence