Bromide ion → Diphenyl sulfide

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence