반응 #58877

반응 방정식

water

1-bromo-3-vinylbenzene

lead tetraacetate

trifluoroacetic acid

→

(3-bromophenyl)acetaldehyde

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGstirred vigorously
2. 2
   여과filtered through a pad of celite
3. 3
   기타The filtrate is separated
4. 4
   세척The filtercake is rinsed with additional portions of dichloromethane
5. 5
   세척The combined organic phases are washed sequentially with water, NaHCO3 and brine
6. 6
   건조dried over MgSO4
7. 7
   농축concentrated in vacuo

실험 절차

A mixture of lead tetraacetate (3.6 g, 8.2 mmol) and trifluoroacetic acid (8.25 mL) at 0° C. is treated dropwise with a solution of 1-bromo-3-vinylbenzene (1.5 g, 8.2 ml) in dichloromethane, allowed to warm to room temperature, stirred for 2 h at room temperature, diluted with dichloromethane, poured into water, stirred vigorously and filtered through a pad of celite. The filtrate is separated. The filtercake is rinsed with additional portions of dichloromethane. The combined organic phases are washed sequentially with water, NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo to afford (3-bromophenyl)acetaldehyde.

출처