Allyl bromide → Methyl-2-allyloxy-5-(4'-fluorophenyl)-benzoate

HRID 442277Notes

Reaction equation

HRID 442277 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:5]=1[OH:17].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[CH:26]=[CH2:27]>CC(C)=O>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:5]=1[O:17][CH2:27][CH:26]=[CH2:25]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 21416429Methyl 4'-fluoro-4-hydroxy-[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 21416435Methyl-2-allyloxy-5-(4'-fluorophenyl)-benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 6.6 g. of methyl-5-(4'-fluorophenyl)-2-hydroxy-benzoate, 5.5 g. of potassium carbonate, 25 ml. of acetone, and 4.5 g. of allyl bromide is heated at reflux for 2 hours, and then stirred at 25° C. overnight. The reaction mixture is partitioned between 100 ml. of water and 100 ml. of ether, the ether solution is dried over magnesium sulfate and concentrated to a thick oil, 6.0 g. This material shows a strong absorption band in the infra-red at 5.75 μ (non-bonded ester) and is homogeneous by thin layer chromatography.

Workup

  1. additionA mixture of 6.6 g
  2. temperatureat reflux for 2 hours
  3. customThe reaction mixture is partitioned between 100 ml
  4. dry with materialof ether, the ether solution is dried over magnesium sulfate
  5. concentrationconcentrated to a thick oil, 6.0 g

Sources & evidence

ORD record
ord-c3c12bcc81d7431784eea7e866879232
Source dataset
uspto-grants-1977_08
Patent number
US04044049

Reaction notes

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