Methyl iodide → Methyl 2-chloro-4,5-difluorobenzoate

HRID 2229386Notes

Reaction equation

HRID 2229386 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](=O)([O-])[O-].[Cs+].[Cs+].IC>CC(C)=O.C(OCC)C>[CH3:13][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([F:12])[C:9]([F:11])=[CH:10][C:2]=1[Cl:1]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 7371712-Chloro-4,5-difluorobenzoic acid

Product 1

HCID 22149760Methyl 2-chloro-4,5-difluorobenzoate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

2-Chloro-4,5-difluorobenzoic acid (1.93 g, 10 mmol) was dissolved in 20 mL of acetone. Cesium carbonate (5.29 g, 15 mmol) was added followed by iodomethane (1.0 mL, 15 mmol). This reaction mixture was heated under reflux for 1 h and then cooled to room temperature. This suspension was then diluted with 40 mL of ethyl ether. The solid was removed by filtration and washed with ethyl ether. The filtrate was evaporated in vacuo to give the title compound in quantitative yield as a clear oil.

Workup

  1. temperatureThis reaction mixture was heated
  2. temperatureunder reflux for 1 h
  3. customThe solid was removed by filtration
  4. washwashed with ethyl ether
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-d48ce28accb1497da254bd2edace6122
Source dataset
uspto-grants-2002_07
Patent number
US06420364B1

Reaction notes

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