Allyl bromide → HCID 20089190, compound

HRID 1492637Notes

Reaction equation

HRID 1492637 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:15][CH:14]=[CH2:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 77580Methyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 20089190HCID 20089190, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 250 mL round-bottom flask equipped with a magnetic stir bar and a reflux condenser was added a solution of 10.33 g (55.4 mmol) of methyl 3-chloro-4-hydroxybenzoate dissolved in 110 mL of acetone and 5.27 mL (60.9 mmol) of allyl bromide and 15.30 g (111 mmol) of powdered potassium carbonate was added. The reaction was stirred and refluxed for 6 hours, then cooled and filtered. The filtrate was evaporated in vacuo and the residue was purified on a silica gel flash chromatography column eluted with 10% EtOAc-hexane to afford 10.462 g (84%) of the title compound.

Workup

  1. customTo a 250 mL round-bottom flask equipped with a magnetic stir bar and a reflux condenser
  2. temperaturerefluxed for 6 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified on a silica gel flash chromatography column
  7. washeluted with 10% EtOAc-hexane

Sources & evidence

ORD record
ord-010d99b38b3b4c629b9bc35360933213
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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