2-Bromopropane → HCID 67618108, compound

HRID 1885895Notes

Reaction equation

HRID 1885895 reaction equation
[Mg].[CH:2](Br)(C)C.[F:6][C:7]([F:17])([F:16])[C:8]1[CH:15]=[CH:14][C:11](C=O)=[CH:10][CH:9]=1.[NH4+].[Cl-].[O:20]1[CH2:24][CH2:23][CH2:22]C1>>[F:17][C:7]([F:6])([F:16])[C:8]1([CH:24]([OH:20])[CH:23]([CH3:2])[CH3:22])[CH:9]=[CH:10][CH:11]=[CH:14][CH2:15]1

Participants

6

Reactant 5

HCID 63582-BromopropaneHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 679964-(Trifluoromethyl)benzaldehydeHCID 5462224Magnesium

Product 1

HCID 67618108HCID 67618108, compoundYield 36.8%

Procedure

To a tetrahydrofuran solution of Grignard reagent prepared from 5.35 g of magnesium and 24.6 g of isopropyl bromide was added under ice-cooling 17.4 g of 4-(trifluoromethyl)benzaldehyde dissolved in tetrahydrofuran, and the mixture was stirred for 30 minutes. The resultant reaction mixture was treated with a saturated NH4Cl aqueous solution and extracted with ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the residue was purified by silica gel column chromatography using n-hexane/dichloromethane to obtain 8.02 g of an oily product of 1-(trifluoromethyl)phenyl-2-methylpropane-1-ol (yield: 36.8%).

Workup

  1. additionwas added under ice-
  2. customThe resultant reaction mixture
  3. extractionextracted with ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4b87827d8f8d460fbc4da5dc663a8007
Source dataset
uspto-grants-1992_09
Patent number
US05147886

Reaction notes

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