Sodium Hydroxide → (2S)-2-(4-bromophenyl)oxirane
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customThe organic layer was separated
- extractionwater layer was extracted with ether
- washCombined organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- 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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