Acetone → 1-(2,4-Difluorophenyl)-2-methylpropan-2-ol

HRID 12103Notes

Reaction equation

HRID 12103 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].[F:5][C:6]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:7]=1[CH2:8][Mg]Br.[Cl-].[NH4+]>C(OCC)C>[F:5][C:6]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:7]=1[CH2:8][C:2]([CH3:4])([OH:3])[CH3:1]

Participants

5

Reactant 3

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 178505754HCID 178505754, compound

Product 1

HCID 220634481-(2,4-Difluorophenyl)-2-methylpropan-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

11.0 mL acetone, diluted with 50 mL diethyl ether, is added dropwise to a solution of 500 mL of 0.25 molar 2,4-difluorobenzylmagnesium bromide in diethyl ether within 20 minutes. Then the mixture is refluxed for 1.5 hours and then hydrolyzed with 10% ammonium chloride solution. The ether phase is separated off, washed with water, dried with sodium sulfate, and evaporated down. The fractional distillation of the residue yields the alcohol as a colorless liquid (boiling point: 70° C.-73° C./2 mmbar). Yield: 20.0 g (86%).

Workup

  1. temperatureThen the mixture is refluxed for 1.5 hours
  2. customThe ether phase is separated off
  3. washwashed with water
  4. dry with materialdried with sodium sulfate
  5. customevaporated down
  6. distillationThe fractional distillation of the residue

Sources & evidence

ORD record
ord-09a95e78dab74866bdc4b0f4e523c6ac
Source dataset
uspto-grants-2010_06
Patent number
US07727984B2

Reaction notes

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