1-(2,3,6-Trifluorophenyl)ethanone → 2-(2,3,6-Trifluorophenyl)propan-2-ol

HRID 2368526Notes

Reaction equation

HRID 2368526 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10](=[O:12])[CH3:11].[CH3:13][Mg]Br>C1COCC1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]([OH:12])([CH3:13])[CH3:11]

Participants

4

Reactant 2

HCID 5942471-(2,3,6-Trifluorophenyl)ethanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 833844992-(2,3,6-Trifluorophenyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2,3,6-trifluorophenyl)ethanone (1.74 g, 10 mmol) in THF (10 mL) was added methyl magnesium bromide (7 mL, 21 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hour. The reaction was quenched by addition of saturated aqueous ammonium chloride and was then extracted with EtOAc. The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford 2-(2,3,6-trifluorophenyl)propan-2-ol. (74).

Workup

  1. customThe reaction was quenched by addition of saturated aqueous ammonium chloride
  2. extractionwas then extracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-d05d134221fc4417be845ad4eeb67297
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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