Allyl iodide → Allyl m-bromophenyl ether

HRID 1370872Notes

Reaction equation

HRID 1370872 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:15](I)[CH:16]=[CH2:17]>CN(C=O)C.C(OCC)(=O)C>[CH2:17]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[CH:16]=[CH2:15]

Participants

6

Reactant 3

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 115633-Bromophenol

Product 1

HCID 257945Allyl m-bromophenyl ether

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

3-Bromophenol (10.0 g, 57.8 mmoles) in anhydrous DMF (60 mL) was treated with K2CO3 (24.0 g, 173 mmoles) and allyl iodide (5.81 mL, 63.6 mmoles). Reaction stirred overnight at 80° C. Reaction allowed to cool to room temperature and diluted with ethyl acetate. The mixture was washed with H2O (2×), brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to provide the title compound with no further purification.

Workup

  1. customReaction
  2. customReaction
  3. temperatureto cool to room temperature
  4. washThe mixture was washed with H2O (2×), brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-da7aa7ea24d14d20944814f7309b46e1
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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