2-(4-Bromophenyl)-2-phenyloxirane → 2-(4-Bromophenyl)-2-phenylacetaldehyde

HRID 509192Notes

Reaction equation

HRID 509192 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=[O:9])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 157379652-(4-Bromophenyl)-2-phenyloxirane

Product 1

HCID 125551782-(4-Bromophenyl)-2-phenylacetaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-(4-bromophenyl)-2-phenyloxirane 51 (5.27 g, 19.15 mmol) and BF3OEt2 (3.29 g, 23.20 mmol) in benzene (50 mL) was shaken vigorously in a separatory funnel for 2 minutes then allowed to stand for 3 minutes. The resulting solution was washed twice with aq. sat. NaHCO3 and the organic layer was separated, dried over Na2SO4 and concentrated to afford 2-(4-bromophenyl)-2-phenylacetaldehyde 52. The crude was used in the next step.

Workup

  1. washThe resulting solution was washed twice with aq. sat. NaHCO3
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a54fb1f46624462e929cf360baaf291a
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

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