反応 #1772045

反応方程式

Magnesium

4-bromo-1,1,1-trifluorobutane

4-bromobenzaldehyde

→

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

収率 82.2%

溶媒

THF

THF

反応条件

後処理

1. 1
   その他The cold bath was removed
2. 2
   温度to warm
3. 3
   workup.STIRRINGstirred 18 h
4. 4
   workup.ADDITIONdiluted with Et2O (1 vol)
5. 5
   その他quenched with sat'd NH4Cl soln
6. 6
   洗浄washed with brine
7. 7
   濃縮Concentrate
8. 8
   workup.ADDITIONcharged to a 40M Biotage® silica gel cartridge
9. 9
   洗浄Gradient elution

実験手順

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%).

出典