1-Bromo-2-Chloroethane → 4-(2-Chloro-ethoxy)-benzoic acid tert-butyl ester

HRID 1840942Notes

Reaction equation

HRID 1840942 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH2:23][Cl:24]>CC(CC(C)C)=O>[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:22][CH2:23][Cl:24])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 117640tert-Butyl 4-hydroxybenzoate

Product 1

HCID 98379994-(2-Chloro-ethoxy)-benzoic acid tert-butyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture containing 0.79 g (4.1 mmol) of 4-hydroxy-benzoic acid tert-butyl ester, 1.13 g (8.14 mmol) of K2CO3 and 1.6 mL (16.3 mmol) of 1-bromo-2-chloro-ethane in 10 mL of isobutyl methyl ketone was refluxed for 5 hours. After filtering, the solvent was removed under reduced pressure affording 0.98 g (94% yield) of 4-(2-chloro-ethoxy)-benzoic acid tert-butyl ester.

Workup

  1. temperaturewas refluxed for 5 hours
  2. filtrationAfter filtering
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2f4742fea31d4cccbc4278c3db0d39ae
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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