반응 #669345

반응 방정식

bromine

triphenylphosphine

alcohol

3(1-trityl-1,2,4-triazol-5-yl)propanol

triethylamine

→

1-bromo-3(1-trityl-1,2,4-triazol-5-yl)propane

수율 43.3%

용매

dichloromethane

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도again maintaining the temperature below 0° C
2. 2
   workup.STIRRINGThe solution was stirred for a further ten minutes
3. 3
   여과filtered through a bed of silica
4. 4
   기타chromatographed on silica

실험 절차

A solution of bromine (5.6 g) in dichloromethane (15 ml) was added dropwise to a stirred solution of triphenylphosphine (9.2 g) in dichloromethane (100 ml) cooled to -5° C. The mixture was stirred for a further ten minutes at 0° C., then treated portionwise with a solution of the above alcohol (6.9 g) and triethylamine (4.9 ml) in dichloromethane (30 ml) again maintaining the temperature below 0° C. The solution was stirred for a further ten minutes, filtered through a bed of silica, then chromatographed on silica, using dichloromethane-ether (25:1) as eluant, to give 1-bromo-3(1-trityl-1,2,4-triazol-5-yl)propane (3.5 g, m.p. 146-149° C.). NMR (CDCl3):δ 1.8(2H,m), 2.15(2H,t), 3.2(2H,t), 7.1-7.3(15H,m), 7.9(1H,s). 13C NMR was used to confirm the position of the trityl substituent.

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