Acetone → HCID 86705532, compound

HRID 2279545Notes

Reaction equation

HRID 2279545 reaction equation
Br[CH2:2][C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[C:7]([F:15])[CH:6]=1)[OH:4].C([O-])([O-])=O.[K+].[K+].CC(C)=O>O>[F:15][C:7]1[CH:6]=[C:5]([C@@H:3]2[CH2:2][O:4]2)[CH:10]=[CH:9][C:8]=1[C:11]([F:14])([F:13])[F:12]

Participants

5

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 86705523HCID 86705523, compound

Product 1

HCID 86705532HCID 86705532, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (R)-2-bromo-1-(3-fluoro-4-(trifluoromethyl)phenyl)ethanol (3.0 g, 10 mmol), K2CO3 (2.9 g, 21 mmol) and acetone (50 mL) and was stirred for 18 h at RT, then poured in H2O and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with hexane/EtOAc (9:1) to afford 2.0 g (93%) of (R)-2-(3-fluoro-4-(trifluoromethyl)phenyl)oxirane (312).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-7f73db11e8d84daf97793a004401ed3f
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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