Allyl bromide → 3-Allyloxy-4-fluoro-benzoic acid methyl ester

HRID 1664229Notes

Reaction equation

HRID 1664229 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([OH:11])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CC(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([O:11][CH2:21][CH:20]=[CH2:19])[CH:5]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 120168924-Fluoro-3-hydroxy-benzoic acid methyl ester

Product 1

HCID 674419363-Allyloxy-4-fluoro-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Fluoro-3-hydroxy-benzoic acid methyl ester (26.3 g, 154.5 mmol) is dissolved in acetone (300 ml). Potassium carbonate (42.7 g, 305.8 mmol) is added, followed 5 minutes later by the addition of allyl bromide (20 ml, 229 mmol). The reaction mixture is stirred overnight at rt, concentrated in vacuo and then diluted with ether and water. The organic layer is washed with saturated brine, dried over sodium sulfate, filtered and concentrated to give the product as a colourless oil.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with ether and water
  3. washThe organic layer is washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-26145d104aaf4099aa0a199aba50c194
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

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