4-Bromoanisole → 1,1,1-Trifluoro-2-(4-methoxyphenyl)propan-2-ol

HRID 414277Notes

Reaction equation

HRID 414277 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([CH3:5])=[O:4].Br[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.[Mg].[Cl-].[NH4+]>CCOCC>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:3]([C:2]([F:7])([F:6])[F:1])([OH:4])[CH3:5])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 77304-BromoanisoleHCID 9871Methyl trifluoromethyl ketoneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 108677871,1,1-Trifluoro-2-(4-methoxyphenyl)propan-2-olYield 94.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1,1,1-Trifluoroacetone (60.4 ml; 675 mmol) dissolved in absolute ether (80 ml) was added, dropwise, at 5° to 10° C. to an ethereal Grignard solution (prepared from p-bromoanisole (84.17 g; 450 mmol) and magnesium (10.9 g; 450 mmol) in ether (600 ml)) and the mixture stirred at room temperature for 20 hours. It was then added to saturated ammonium chloride solution, extracted with ether and the extract washed with water, dried over sodium sulphate and concentrated. The precipitate was filtered off washed with hexane and the filtrate concentrated. 1-(4-methoxyphenyl)-1-trifluoromethylethanol (93.35 g=94.2% of theory) was obtained as a brown oil that was used without further purification. (The alcohol can also be coverted direct to the nitrile in a one-pot reaction.

Workup

  1. additionwas added
  2. extractionextracted with ether
  3. washthe extract washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. filtrationThe precipitate was filtered off
  7. washwashed with hexane
  8. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-2b9742ff518746cda980bde87d8656f2
Source dataset
uspto-grants-1988_12
Patent number
US04791123

Reaction notes

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