4-Bromophenol → 1-Bromo-4-(ethenyloxy)benzene

HRID 2068545Notes

Reaction equation

HRID 2068545 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH:9](OC(=O)C)=[CH2:10].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]=[CH2:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 7904Vinyl AcetateHCID 10340Sodium Carbonate

Product 1

HCID 114013721-Bromo-4-(ethenyloxy)benzeneYield 74%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-bromophenol (75 g, 433.5 mmol), acetic acid ethenyl ester (80.5 mL, 867.0 mmol) and sodium carbonate (27.6 g, 260.10 mmol) in toluene (430 mL) add di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)diiridium (2.9 g, 4.34 mmol) and the heat the mixture at 100° C. for 2.5 hours. Cool the mixture to ambient temperature, dilute with ethyl acetate (EtOAc) (300 mL) and wash once with water (400 mL). Separate the organic portion and wash once with brine (250 mL). Dry the material over sodium sulfate, filter, and concentrate under reduced pressure. Purify the crude mixture by flash chromatography (0% to 5% EtOAc/Hex) to give the title compound (63.5 g, 74%): GCMS: 198.

Workup

  1. temperatureCool the mixture to ambient temperature
  2. washwash once with water (400 mL)
  3. customSeparate the organic portion
  4. washwash once with brine (250 mL)
  5. dry with materialDry the material over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the crude mixture by flash chromatography (0% to 5% EtOAc/Hex)

Sources & evidence

ORD record
ord-05b90f228a624feaa054dc1e3b317689
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

Loading…