Toluene → (2S)-2-(3,4-Difluorophenyl)oxirane

HRID 2060959

Reaction equation

HRID 2060959 reaction equation
Cl[CH2:2][C@H:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([F:12])[CH:6]=1)[OH:4].C1(C)C=CC=CC=1.[OH-].[Na+]>O>[F:12][C:7]1[CH:6]=[C:5]([C@H:3]2[CH2:2][O:4]2)[CH:10]=[CH:9][C:8]=1[F:11]

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 25324204(alphaS)-alpha-(Chloromethyl)-3,4-difluorobenzenemethanol

Product 1

HCID 30070539(2S)-2-(3,4-Difluorophenyl)oxiraneYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of (1S)-2-chloro-1-(3,4-difluorophenyl)-1-ethanol (net 11.47 g, 59.5 mmol), toluene (25.23 g), sodium hydroxide (2.53 g, 1.06 molar equivalents) and water (24.25 g) was stirred and heated at 40° C. for 1 hour. The organic layer was separated, washed with water, and concentrated under reduced pressure. (2S)-2-(3,4-difluorophenyl)oxirane was obtained as resultant concentrate (net 8.94 g, yield: 96%).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8b8680fcb55a40d3bd87b75739f78f66
Source dataset
uspto-grants-2012_10
Patent number
US08278475B2

Linked notes

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