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 dimethylformamide and, with stirring at about 20° C., 13.0 g of polyprenyl bromide of general formula (II) in which n=15 and A=Br were 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 the eluent to give 8.6 g of a slightly yellow liquid. NMR analysis of this liquid showed that a signal (doublet, δ=3.91) assignable to --CH2Br of the starting polyprenyl bromide had disappeared and a signal (doublet, δ=3.47) assignable to --CH2S-- and a signal (multiplet, δ=7.05- 7.32) assignable to --SC6H5 had newly appeared. FD-MASS analysis gave m/e=1334.

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

ORD record

ord-57ec829936404bfc875329c5947beb2f

Source dataset

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04603208