3-Bromo-5-(trifluoromethyl)benzaldehyde → 1-(3-Bromo-5-(trifluoromethyl)phenyl)ethanol

HRID 534847Notes

Reaction equation

HRID 534847 reaction equation
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[CH:8]=[O:9]>C1COCC1>[Br:4][C:5]1[CH:6]=[C:7]([CH:8]([OH:9])[CH3:1])[CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1

Participants

4

Reactant 2

HCID 161154383-Bromo-5-(trifluoromethyl)benzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 579802001-(3-Bromo-5-(trifluoromethyl)phenyl)ethanolYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution at −10° C. of methyl magnesium bromide (38.00 mL, 3.0 M in ethyl ether, 114.0 mmol) in THF (200.0 mL) was added dropwise a solution of 3-bromo-5-(trifluoromethyl)benzaldehyde (Reference Example 39, 22.01 g, 86.98 mmol) in THF (100 mL) and after the addition was complete, the reaction mixture was held at −10° C. for 2 h. After this time, the reaction was quenched with saturated ammonium hydrochloride (300.0 mL) and warmed to room temperature. The reaction mixture was diluted with ethyl acetate, washed with water, and saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure to provide 1-(3-bromo-5-(trifluoromethyl)phenyl)ethanol (21.30 g, 91%) as a pale yellow oil.

Workup

  1. additionafter the addition
  2. customAfter this time, the reaction was quenched with saturated ammonium hydrochloride (300.0 mL)
  3. additionThe reaction mixture was diluted with ethyl acetate
  4. washwashed with water, and saturated sodium chloride
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea9d85682b224a5d969c32482e76a82f
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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