Potassium Carbonate → Methyl 2-(2-bromo-4-chlorophenoxy)propanoate

HRID 2390312Notes

Reaction equation

HRID 2390312 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH3:10][O:11][C:12](=[O:16])[CH:13](Br)[CH3:14].C([O-])([O-])=O.[K+].[K+]>COCCOC>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH:13]([CH3:14])[C:12]([O:11][CH3:10])=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696702-Bromo-4-chlorophenolHCID 95576Methyl 2-bromopropionate

Product 1

HCID 20526233Methyl 2-(2-bromo-4-chlorophenoxy)propanoate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-bromo-4-chlorophenol (250 mg; 1.21 mmol) and methyl-2-bromopropionate (VWR; 135 μL, 1.21 mmol) in DME (5 mL) was treated with K2CO3 (250 mg, 1.81 mmol) and refluxed for 18 hours. The reaction mixture was filtered, the filtrate was concentrated and purified by flash column chromatography (silica), eluting with heptane containing increasing amounts of EtOAc. The title compound was obtained as a yellow liquid (306 mg; 87%).

Workup

  1. temperaturerefluxed for 18 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. custompurified by flash column chromatography (silica)
  5. washeluting with heptane containing
  6. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-cf158fd43e444381a55ae68e93146512
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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