Sodium Hydroxide → (2S)-2-(4-bromophenyl)oxirane

HRID 424412Notes

Reaction equation

HRID 424412 reaction equation
[OH-].[Na+].Br[CH2:4][C@H:5]([C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)[OH:6]>C(OCC)C>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C@H:5]2[CH2:4][O:6]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11097916(s)-2-Bromo-1-(4-bromophenyl)ethanol

Product 1

HCID 12163514(2S)-2-(4-bromophenyl)oxiraneYield 100.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Aqueous sodium hydroxide (1M, 400 ml) was added to 2-bromo-(1S)-1-(4-bromophenyl)ethanol (77.0 g) in diethyl ether (400 ml) and stirred at room temperature for 5 hours. The organic layer was separated and water layer was extracted with ether. Combined organic layer was washed with brine and dried over anhydrous sodium sulfate. Removal of the solvent yielded (2S)-2-(4-bromophenyl)oxirane (55.0 g) as a pale brown oil.

Workup

  1. customThe organic layer was separated
  2. extractionwater layer was extracted with ether
  3. washCombined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-a2eb469c71b94d8f968070d6e48d7265
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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