Potassium Carbonate → Methyl 2-fluoro-6-iodobenzoate

HRID 2174682Notes

Reaction equation

HRID 2174682 reaction equation
[C:1](Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([I:17])[C:9]=1[C:10]([OH:12])=[O:11].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.CN(C=O)C.CO>[F:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([I:17])[C:9]=1[C:10]([O:12][CH3:1])=[O:11]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 27333022-Fluoro-6-iodobenzoic acid

Product 1

HCID 12192164Methyl 2-fluoro-6-iodobenzoate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (2.5 ml, 28.66 mmol, 1.5 eq.) was added at room temperature to a suspension of 2-fluoro-6-iodobenzoic acid (5.1 g, 19.17 mmol, 1 eq.) in 40 ml of dry DCM under nitrogen atmosphere. A few drops of dry DMF were added and the mixture was stirred at room temperature for 1 h. The solvent was removed by distillation. The obtained residue was taken up in acetonitrile, which was distilled again, to remove excess acidity. The resulting brown oil was dissolved in dry DCM and the resulting solution was dropwise added to a suspension of potassium carbonate (7 g, 50.6 mmol, 2.6 eq.) in 20 ml of dry methanol. The reaction mixture was then stirred at room temperature overnight.

Workup

  1. customThe solvent was removed by distillation
  2. distillationwhich was distilled again
  3. customto remove excess acidity
  4. dissolutionThe resulting brown oil was dissolved in dry DCM
  5. stirringThe reaction mixture was then stirred at room temperature overnight

Sources & evidence

ORD record
ord-1f13627598b041dba4ae8b9661d3fb66
Source dataset
uspto-grants-2015_06
Patent number
US09062033B2

Reaction notes

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