반응 #833473

반응 방정식

thiophenol

potassium carbonate

dimethylformamide

bromide

bromide

→

phenyl sulfide

용매

water

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.STIRRINGthe mixture was stirred overnight at room temperature
3. 3
   추출extracted with hexane
4. 4
   세척The hexane layer was washed with a 10% aqueous solution of sodium hydroxide and water
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe hexane was distilled off
7. 7
   기타to give a yellow liquid
8. 8
   기타The yellow liquid was purified by silica gel column chromatography
9. 9
   기타to give 8.6 g of a slightly yellow liquid
10. 10
    기타FD-MASS analysis gave m/e=1334

실험 절차

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.

출처