Carbon Disulfide → Benzyl (4-phenyl)dithiobenzoate

Participants

Reaction Conditions

Reaction Steps

In 50 mL of dry tetrahydrofuran, 204 mL of (4-phenyl)phenyl magnesium bromide (a 0.5M tetrahydrofuran solution) was added, and the resulting mixture was stirred and then cooled to 0° C. While keeping 0° C., 7.77 g of carbon disulfide was added over 15 minutes, and the resulting mixture was stirred at 0° C. for 1 hour. Subsequently, 15.86 g of benzyl bromide was added over 15 minutes, and the resulting mixture was stirred at room temperature for 1 hour. After adding 300 mL of ice water, the organic layer was extracted with 500 mL of ethyl acetate. Furthermore, the organic layer was washed with 300 mL of brine and dried over anhydrous magnesium sulfate. The anhydrous magnesium sulfate was removed by filtration, and the residual solvent was then removed. The residue was purified on silica gel (ethyl acetate/hexane solvent) to obtain benzyl (4-phenyl)dithiobenzoate (28.4 g, yield: 87%) (exchange-chain transfer type RAFT agent).

Provenance & Evidence