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

HRID 353979Notes

Reaction equation

HRID 353979 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-6de3873b9a454f918ed6e44cec1334c6
Source dataset
uspto-grants-2004_06
Patent number
US06756372B2

Reaction notes

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