Oxalyl chloride → Methyl 2,6-dichloro-5-fluoronicotinate

HRID 1810979Notes

Reaction equation

HRID 1810979 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C)C=O>[CH3:13][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([F:12])[C:9]([Cl:11])=[N:10][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27336592,6-Dichloro-5-fluoronicotinic acid

Product 1

HCID 2775354Methyl 2,6-dichloro-5-fluoronicotinate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,6-dichloro-5-fluoro-nicotinic acid (1.00 g, 4.46 mmol) in methylene chloride is added of oxalyl chloride (50 mL, 0.445 mL, 5.30 mmol) followed by 2 drops of N,N-dimethylformamide. Vigorous bubbling is observed and the mixture is stirred at room temperature for 1 h. The reaction mixture is concentrated under reduced pressure and the residue is taken back up into methylene chloride (50 mL). To the solution is added MeOH (20 mL) and the mixture is stirred at room temperature for 2 h. The reaction mixture is concentrated under reduced pressure to provide 2,6-dichloro-5-fluoro-nicotinic acid methyl ester as an oil.

Workup

  1. customVigorous bubbling
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. additionTo the solution is added MeOH (20 mL)
  4. stirringthe mixture is stirred at room temperature for 2 h
  5. concentrationThe reaction mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-589159f313554ffb8f37cf7d2e1b0b43
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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