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

HRID 1091355
Notes
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Reaction equation

HRID 1091355 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 aqueous layer was extracted with ether. The 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. extractionaqueous layer was extracted with ether
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-339c6f5186ae4c92b386345a07b37205
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129377B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes