Réaction #1772045

Équation de réaction

Magnesium

4-bromo-1,1,1-trifluorobutane

4-bromobenzaldehyde

→

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

Rendement 82.2%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   AutreThe cold bath was removed
2. 2
   Températureto warm
3. 3
   workup.STIRRINGstirred 18 h
4. 4
   workup.ADDITIONdiluted with Et2O (1 vol)
5. 5
   Autrequenched with sat'd NH4Cl soln
6. 6
   Lavagewashed with brine
7. 7
   ConcentrationConcentrate
8. 8
   workup.ADDITIONcharged to a 40M Biotage® silica gel cartridge
9. 9
   LavageGradient elution

Mode opératoire

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%).

Source