반응 #7729

반응 방정식

water

N-bromosuccinimide

triphenylphosphine

ethyl [(4-hydroxy-2-pyrimidinyl)thio]acetate

→

Ethyl [(4-bromo-2-pyrimidinyl)thio]acetate

용매

dioxane

반응 조건

후처리

1. 1
   온도with cooling
2. 2
   온도the mixture is heated
3. 3
   온도at reflux for 45 min
4. 4
   추출is then extracted 3× with in each case 300 ml of methyl tert-butyl ketone
5. 5
   세척The organic phase is washed 2× with water and 1× with concentrated NaCl solution
6. 6
   건조dried over magnesium sulphate
7. 7
   농축concentrated
8. 8
   workup.STIRRINGThe residue is stirred in 60 ml of methyl tert-butyl ketone
9. 9
   여과filtered off
10. 10
    농축The mother liquor is concentrated
11. 11
    기타the residue is purified by silica gel chromatography (dichloromethane)

실험 절차

Under argon, 52.5 g (0.20 mol) of triphenylphosphine are initially charged in 600 ml of dioxane, and 35.6 g (0.20 mol) of N-bromosuccinimide are added a little at a time, with cooling. The mixture is stirred at RT for 30 min. 8.6 g (0.04 mol) of ethyl [(4-hydroxy-2-pyrimidinyl)thio]acetate are then added and the mixture is heated at reflux for 45 min. A total of 2 l of water are added to the mixture, which is then extracted 3× with in each case 300 ml of methyl tert-butyl ketone. The organic phase is washed 2× with water and 1× with concentrated NaCl solution, dried over magnesium sulphate and concentrated. The residue is stirred in 60 ml of methyl tert-butyl ketone and filtered off. The mother liquor is concentrated and the residue is purified by silica gel chromatography (dichloromethane).

출처