반응 #73504

반응 방정식

2

N-ethyl-6-[3-methyl-5-oxo-4-(pyridin-3-ylmethyl)-2,5-dihydro-1H-pyrazol-1-yl]-N-phenylpyridine-3-sulfonamide hydrochloride

[3-(methoxymethyl)phenyl]methanol

MeOH

phosphorus tribromide

→

1-(bromomethyl)-3-(methoxymethyl)benzene

수율 39.0%

용매

Et2O

반응 조건

후처리

1. 1
   기타The crude reaction mixture
2. 2
   기타After evaporating off the MeOH under reduced pressure
3. 3
   추출the aqueous phase is extracted with DCM (2×200 mL)
4. 4
   건조dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue obtained
8. 8
   기타is purified by chromatography on a column of silica gel
9. 9
   세척eluting with a cyclohexane/EtOAc gradient of 0 to 20% EtOAc

실험 절차

To a solution of 5.91 g (38.8 mmol) of 2 [3-(methoxymethyl)phenyl]methanol in 75 mL of Et2O are added dropwise, at 0° C., 9.1 mL (97.1 mmol) of phosphorus tribromide. The reaction mixture is allowed to warm slowly to room temperature and stirring is continued for 4 hours. The crude reaction mixture is then poured cautiously into a mixture of 100 g of ice and 100 mL of MeOH. After evaporating off the MeOH under reduced pressure, the aqueous phase is extracted with DCM (2×200 mL). The organic phases are combined, dried over Na2SO4, filtered and then concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 20% EtOAc. 3.25 g of 1-(bromomethyl)-3-(methoxymethyl)benzene are thus obtained in the form of an oil.

출처