Bromide ion → Diphenyl sulfide

Temperature

20 °C

2.2 g of thiophenol and 2.8 g of potassium carbonate were added to 50 ml of N,N-dimethylformamide, and with stirring at about 20° C., 13.0 g of polyprenylbromide of general formula (II) in which n is 15 and A2 is Br was added dropwise. After the addition, the mixture was stirred overnight at room temperature. The reaction mixture was poured into about 100 ml of water and extracted with hexane. The hexane layer was washed with a 10% aqueous solution of sodium hydroxide and water, and then dried over anhydrous magnesium sulfate. The hexane was distilled off to give a yellow liquid. The yellow liquid was purified by silica gel column chromatography using methylene chloride as an eluent to give 8.6 g of a slightly yellow liquid. The NMR analysis of this liquid showed that a signal (doublet, δ=3.91) assigned to --CH2Br of the starting polyprenyl bromide disappeared, and a signal (doublet, δ=3.47) assigned to a --CH2S-- and a signal (multiplet, δ=7.05-7.32) assigned to --SC6H5 newly appeared. The FD-MASS analysis gave m/e=1334.

1. additionwas added dropwise
2. additionAfter the addition
3. stirringthe mixture was stirred overnight at room temperature
4. extractionextracted with hexane
5. washThe hexane layer was washed with a 10% aqueous solution of sodium hydroxide and water
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationThe hexane was distilled off
8. customto give a yellow liquid
9. customThe yellow liquid was purified by silica gel column chromatography
10. customto give 8.6 g of a slightly yellow liquid
11. customThe FD-MASS analysis gave m/e=1334

ORD record

ord-39caf9370e9342a48212bb725fc3e857

Source dataset

uspto-grants-1991_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05077046