Allyl bromide → HCID 14838649, compound

HRID 893715Notes

Reaction equation

HRID 893715 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:12][C:4]1[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 327085Methyl 4-chloro-2-hydroxybenzoate

Product 1

HCID 14838649HCID 14838649, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 4-chloro-2-hydroxybenzoate (2f) (96.3 g, 0.52 mol), allyl bromide (134 ml, 1.55 mol) and ground potassium carbonate (107 g, 0.77 mol) in 1500 ml of dry acetone was heated under reflux for 20 hours. The inorganic salt was removed by filtration, and the solvent and excess allyl bromide evaporated to dryness to give 3f (117 g, 99.6% yield) as a yellow solid, mp 47°-55° C. NMR (CDCl3) δ 7.73 (d, 1H, J=8 Hz, aromatic proton meta to Cl), 6.97 (m, 2H, aromatic protons alpha to Cl), 6.40-5.17 (m, 3H, olefinic orotons), 4.57 (m, 2H, CH2) and 3.90 (s, 3H, CH3).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. customThe inorganic salt was removed by filtration
  4. customthe solvent and excess allyl bromide evaporated to dryness

Sources & evidence

ORD record
ord-fdc21034708e49c4b64db7f57afef9eb
Source dataset
uspto-grants-1992_06
Patent number
US05126364

Reaction notes

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