Allyl bromide → 3-Allyloxy-4-chloro-benzoic acid ethyl ester

HRID 2064778Notes

Reaction equation

HRID 2064778 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[CH2:8][CH:9]=[CH2:10].[CH2:11]([O:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([OH:22])[CH:16]=1)[CH3:12]>CC(C)=O>[CH2:11]([O:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([O:22][CH2:10][CH:9]=[CH2:8])[CH:16]=1)[CH3:12]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 58847555Ethyl 4-chloro-3-hydroxybenzoate

Product 1

HCID 669987863-Allyloxy-4-chloro-benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

K2CO3 (78.5 mmol) and 3-bromo-1-propen (52.3 mmol) are added to a solution of 4-chloro-3-hydroxy-benzoic acid ethyl ester (26.2 mmol) in acetone (50 mL). The mixture is heated to reflux for 16 h and cooled to RT. The solvents are removed in vacuo to give the desired product which is used without further purification. LC-MS: tR=1.05 min; [M+H]+=240.9.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 16 h
  3. customThe solvents are removed in vacuo

Sources & evidence

ORD record
ord-f721484761314cf0bd182e6316f9dab7
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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