Benzyl Bromide → 4-Benzyloxy-2-chloro-benzoic acid ethyl ester

HRID 1442479

Reaction equation

HRID 1442479 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[Cl:12])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(C(C)=O)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:7][C:6]=1[Cl:12])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 19981058Ethyl 2-chloro-4-hydroxybenzoate

Product 1

HCID 684205954-Benzyloxy-2-chloro-benzoic acid ethyl esterYield 86.9%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

16.76 g (83.5 mmol) of 2-chloro-4-hydroxy-benzoic acid ethyl ester and 23.1 g (167 mmol) of potassium carbonate were added to 100 mL of methyl ethyl ketone followed by the addition of 17.1 g (100 mmol) of bromomethylbenzene while stirring. After refluxing for 28 hours, the mixture was cooled and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography to obtain 21.1 g of a light yellow solid.

Workup

  1. temperatureAfter refluxing for 28 hours
  2. temperaturethe mixture was cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-effc506ca556489ca6822db551cfe537
Source dataset
uspto-grants-2010_02
Patent number
US07658979B2

Linked notes

Loading…