반응 #564462

반응 방정식

thiophenol

potassium carbonate

N,N-dimethylformamide

bromide

→

phenyl sulfide

용매

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONAfter the addition
3. 3
   workup.STIRRINGthe mixture was stirred overnight at room temperature
4. 4
   추출extracted with hexane
5. 5
   세척The hexane layer was washed with a 10% aqueous solution of sodium hydroxide and water
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe hexane was distilled off
8. 8
   기타to give a yellow liquid
9. 9
   기타The yellow liquid was purified by silica gel column chromatography
10. 10
    기타to give 8.6 g of a slghtly yellow liquid
11. 11
    기타The FD-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 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 ws 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 slghtly 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 --CH2S-- and a signal (multiplet, δ= 7.05-7.32) assigned to --SC6H5 newley appeared. The FD-MASS analysis gave m/e=1334.

출처