4-Bromobenzaldehyde → HCID 67266122, compound

HRID 1684863Notes

Reaction equation

HRID 1684863 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][C:6]([F:9])([F:8])[F:7].[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1>C1COCC1>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]([OH:16])[CH2:3][CH2:4][CH2:5][C:6]([F:9])([F:8])[F:7])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 707414-BromobenzaldehydeHCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 5462224Magnesium

Product 1

HCID 67266122HCID 67266122, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
24 °C

Procedure

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%).

Workup

  1. customThe cold bath was removed
  2. temperatureto warm
  3. stirringstirred 18 h
  4. additiondiluted with Et2O (1 vol)
  5. customquenched with sat'd NH4Cl soln
  6. washwashed with brine
  7. concentrationConcentrate
  8. additioncharged to a 40M Biotage® silica gel cartridge
  9. washGradient elution

Sources & evidence

ORD record
ord-381964c8b7fd4185ac23769bb2c99b53
Source dataset
uspto-grants-2012_04
Patent number
US08147818B2

Reaction notes

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