3',5'-Difluoroacetophenone → 2-(3,5-Difluorophenyl)propan-2-ol

HRID 1499589Notes

Reaction equation

HRID 1499589 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[CH3:12][Mg]Br>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]([OH:11])([CH3:12])[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 5185963',5'-DifluoroacetophenoneHCID 178418573HCID 178418573, compound

Product 1

HCID 577321592-(3,5-Difluorophenyl)propan-2-olYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a solution of 1-(3,5-difluorophenyl)ethanone (2.00 g, 12.8 mmol) in THF (20 mL) at 0-5° C., methylmagnesium bromide in THF (3.0 M; 5.12 mL, 15.4 mmol) was added dropwise. The mixture was stirred at 0-5° C. for 1 h, then quenched with brine, extracted with EtOAc (2 times). The combined organic phases were washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to give the sub-title compound as a colorless oil (2.12 g, 96.1%).

Workup

  1. customquenched with brine
  2. extractionextracted with EtOAc (2 times)
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fdae6641037a416abc047e69161e871f
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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