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

HRID 1694680Notes

Reaction equation

HRID 1694680 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[Br:10][C:11]1[CH:16]=[CH:15][C:14](O)=[C:13]([Cl:18])[CH:12]=1.C(=O)([O-])[O-:20].[K+].[K+]>CN(C=O)C>[C:6]([O:5][C:3](=[O:4])[CH2:2][O:20][C:16]1[CH:15]=[CH:14][C:13]([Cl:18])=[CH:12][C:11]=1[Br:10])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 198594-Bromo-2-chlorophenolHCID 79177tert-Butyl bromoacetate

Product 1

HCID 49766393tert-Butyl (2-bromo-4-chlorophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl bromoacetate (2.6 ml) was added to a stirred mixture of 4-bromo-2-chlorophenol (3 g) and potassium carbonate (6.2 g) in DMF (40 ml) at RT. After 16 h the reaction was partitioned between diethylether and water, the organics separated, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 4% EtOAc/iso-hexane. Yield 4.05 g

Workup

  1. customAfter 16 h the reaction was partitioned between diethylether and water
  2. customthe organics separated, dried
  3. customevaporated under reduced pressure
  4. customThe residue was purified by chromatography on silica eluting with 4% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-4ce422a72fa0426a88545ef9414951de
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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