Acetonitrile → 3-[(4-Bromophenoxy)methyl]-4-penten-1-ol

반응식

[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].Cl[CH2:8]/[CH:9]=[CH:10]/[CH2:11]Cl.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.[Cl-].[NH4+].[C:23](#N)C>>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:8][CH:9]([CH:10]=[CH2:11])[CH2:23][CH2:1][OH:4])=[CH:16][CH:15]=1

참가 물질

반응물 5

HCID 6342Acetonitrile

HCID 78084-Bromophenol

HCID 10796Cesium carbonate

HCID 25517Ammonium Chloride

HCID 6421971,4-Dichloro-2-butene, (2E)-

생성물 1

HCID 181732583-[(4-Bromophenoxy)methyl]-4-penten-1-ol

실험 절차

80 mmol (17.4 g) of caesium carbonate are added to a solution, cooled to 0° C., of 80 mmol (10 g) of trans-1,4-dichloro-2-butene and 53.3 mmol (9.23 g) of para-bromophenol in 500 ml of acetonitrile, and then the mixture is stirred at ambient temperature for 4 days. The mixture is hydrolysed with 250 ml of a saturated aqueous solution of ammonium chloride and then extracted with ethyl acetate. The organic phases are combined and washed with a saturated aqueous solution of sodium chloride and then dried over magnesium sulphate. After evaporation, the expected product is obtained following purification by chromatography on silica gel using a 98:2 petroleum ether/ethyl acetate mixture as eluant.