반응 #1772045

반응 방정식

Magnesium

4-bromo-1,1,1-trifluorobutane

4-bromobenzaldehyde

→

1-(4-bromophenyl)-5,5,5-trifluoropentan-1-ol

수율 82.2%

용매

THF

THF

반응 조건

후처리

1. 1
   기타The cold bath was removed
2. 2
   온도to warm
3. 3
   workup.STIRRINGstirred 18 h
4. 4
   workup.ADDITIONdiluted with Et2O (1 vol)
5. 5
   기타quenched with sat'd NH4Cl soln
6. 6
   세척washed with brine
7. 7
   농축Concentrate
8. 8
   workup.ADDITIONcharged to a 40M Biotage® silica gel cartridge
9. 9
   세척Gradient elution

실험 절차

Magnesium (0.636 g, 26.2 mmol) was added to a solution of 4-bromo-1,1,1-trifluorobutane (5 g, 26.2 mmol) in THF (100 mL) and under nitrogen. The solution was stirred for 18 h at 24° C., and the Grignard reagent was transferred via cannula to a solution of 4-bromobenzaldehyde (4.85 g, 26.2 mmol) in THF (50 mL) at −78° C. under nitrogen. The cold bath was removed and the reaction allowed to warm and stirred 18 h, diluted with Et2O (1 vol), quenched with sat'd NH4Cl soln, and washed with brine. Concentrate, take up in CH2Cl2 and charged to a 40M Biotage® silica gel cartridge. Gradient elution was performed from 15% to 100% B over 1 L (A/B Hexanes/EtOAc) to give 1-(4-bromophenyl)-5,5,5-trifluoropentan-1-ol 6.4 g (82%).

출처