Water → Ethyl 2-(2-bromo-4-chlorophenoxy)-2-methylpropanoate

HRID 2390313Notes

Reaction equation

HRID 2390313 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10]([O:12][C:13](=[O:18])[C:14](Br)([CH3:16])[CH3:15])[CH3:11].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][C:14]([CH3:16])([CH3:15])[C:13]([O:12][CH2:10][CH3:11])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 696702-Bromo-4-chlorophenol

Product 1

HCID 58243827Ethyl 2-(2-bromo-4-chlorophenoxy)-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-bromo-4-chlorophenol (250 mg; 1.21 mmol) and ethyl-2-bromoisobutyrate (450 μl; 3.0 mmol) in DMF (5 mL) was treated with K2CO3 (250 mg, 1.81 mmol) and heated at 120° C. for 4.5 hours. Water was added and the reaction mixture was extracted 3 times with EtOAc. The combined organic phases were dried over MgSO4, filtered, concentrated and purified by flash column chromatography (silica), eluting with heptane containing increasing amounts of EtOAc. The title compound was obtained as a yellow sticky solid (320 mg; 83%).

Workup

  1. extractionthe reaction mixture was extracted 3 times with EtOAc
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (silica)
  6. washeluting with heptane containing
  7. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-789cd7d398834abdb97b10e3bfd174f5
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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