반응 #1138534

반응 방정식

4-bromo-1-chloro-2-fluorobenzene

magnesium

(R,E)-2-methyl-N-((1-methyl-1H-pyrazol-4-yl)methylene)propane-2-sulfinamide

→

(R)—N—((S)-(4-chloro-3-fluorophenyl)(1-methyl-1H-pyrazol-4-yl)methyl)-2-methylpropane-2-sulfinamide

수율 45.1%

용매

THF

반응 조건

후처리

1. 1
   온도After cooling to −78° C.
2. 2
   workup.STIRRINGstirred at −78° C. for 6 h
3. 3
   기타The reaction was quenched with aq. NH4Cl solution
4. 4
   추출extracted with EtOAc
5. 5
   건조The combined organic layers were dried (MgSO4)
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타The crude product was purified by SiO2 chromatography
9. 9
   세척eluting with DCM/MeOH (150:1)

실험 절차

To a mixture of 4-bromo-1-chloro-2-fluorobenzene (11.7 g, 56.0 mmol) and magnesium turnings (2.1 g, 84 mmol) in THF (150 mL) at RT was added a few drops of 1,2-dibromoethane (1.1 g, 5.6 mmol). The mixture was stirred at RT for 1.5 h. After cooling to −78° C., (R,E)-2-methyl-N-((1-methyl-1H-pyrazol-4-yl)methylene)propane-2-sulfinamide (4.00 g, 18.7 mmol) was added and stirred at −78° C. for 6 h. The reaction was quenched with aq. NH4Cl solution and extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered, and concentrated. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (150:1) to afford the 2.9 g (45%) of (R)—N—((S)-(4-chloro-3-fluorophenyl)(1-methyl-1H-pyrazol-4-yl)methyl)-2-methylpropane-2-sulfinamide (48). LCMS (ESI) m/z: 344.1 [M+H]+.

출처