Carbon Disulfide → Benzyl (4-phenyl)dithiobenzoate

Temperature

0 °C

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).

1. customWhile keeping 0° C.
2. stirringthe resulting mixture was stirred at 0° C. for 1 hour
3. stirringthe resulting mixture was stirred at room temperature for 1 hour
4. extractionthe organic layer was extracted with 500 mL of ethyl acetate
5. washFurthermore, the organic layer was washed with 300 mL of brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe anhydrous magnesium sulfate was removed by filtration
8. customthe residual solvent was then removed
9. customThe residue was purified on silica gel (ethyl acetate/hexane solvent)

ORD record

ord-047dd168e653488f89b31c8c6fa89d68

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08182975B2