3,4,5-Trifluorobenzaldehyde → (R)-1-(3,4,5-Trifluorophenyl)ethanol

HRID 424016Notes

Reaction equation

HRID 424016 reaction equation
[CH3:1][Mg+].[Br-].[F:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([F:14])[C:12]=1[F:13])[CH:8]=[O:9]>C1COCC1>[F:4][C:5]1[CH:6]=[C:7]([CH:8]([OH:9])[CH3:1])[CH:10]=[C:11]([F:14])[C:12]=1[F:13]

Participants

4

Reactant 2

HCID 27769543,4,5-TrifluorobenzaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 59386327(R)-1-(3,4,5-Trifluorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An ethereal solution (17.41 ml, 52.24 mmol, 3M) of MeMgBr was slowly added at −78° C. to a solution of 3,4,5-trifluorobenzaldehyde (6.96 g, 43.53 mmol) in THF (125 ml). The reaction mixture was stirred at room temperature for 16 h and was cooled (0° C.) and was quenched, sequentially, with excess ethyl acetate (10 ml) and water (5 ml). Excess anhydrous MgSO4 (5 g) was added and stirred for 30 minutes at room temperature. The suspension was filtered over celite and the solids were washed with ethyl acetate (2×25 ml). The combined filtrate was evaporated to obtain the product in quantitative yield (7.65 g).

Workup

  1. temperaturewas cooled (0° C.)
  2. customwas quenched
  3. additionExcess anhydrous MgSO4 (5 g) was added
  4. stirringstirred for 30 minutes at room temperature
  5. filtrationThe suspension was filtered over celite
  6. washthe solids were washed with ethyl acetate (2×25 ml)
  7. customThe combined filtrate was evaporated
  8. customto obtain the product in quantitative yield (7.65 g)

Sources & evidence

ORD record
ord-0ed51421be164c9faddace59a5675b2f
Source dataset
uspto-grants-2012_01
Patent number
US08101799B2

Reaction notes

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