Potassium Carbonate → tert-Butyl (2-bromo-4-chlorophenoxy)acetate

HRID 2390104Notes

Reaction equation

HRID 2390104 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>CC(C)=O>[C:21]([O:20][C:18](=[O:19])[CH2:17][O:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Br:1])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696702-Bromo-4-chlorophenolHCID 79177tert-Butyl bromoacetate

Product 1

HCID 49766393tert-Butyl (2-bromo-4-chlorophenoxy)acetateYield 95.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-bromo-4-chlorophenol (Aldrich; 13.11 g; 63.2 mmol) in acetone (100 mL) was treated with potassium carbonate (9.61 g; 69.5 mmol), stirred for 10 minutes then treated with tert-butyl bromoacetate (Aldrich; 9.34 mL; 63.2 mmol). The reaction mixture was stirred at 65° C. for 18 hours, then the mixture was filtered, the solid was washed with acetone and the filtrate was concentrated to dryness under vacuum to give the title compound as a yellow sticky solid (19.4 g, 95%).

Workup

  1. stirringThe reaction mixture was stirred at 65° C. for 18 hours
  2. filtrationthe mixture was filtered
  3. washthe solid was washed with acetone
  4. concentrationthe filtrate was concentrated to dryness under vacuum

Sources & evidence

ORD record
ord-273dad7c225042c9bf4765189c9f64a3
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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