Oxalyl chloride → 2-Fluoro-4-formylbenzoyl chloride

HRID 2075186Notes

Reaction equation

HRID 2075186 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:16])=O>CN(C=O)C.CO>[F:1][C:2]1[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 184419582-Fluoro-4-formylbenzoic acid

Product 1

HCID 584152862-Fluoro-4-formylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 887MethanolSolvent

Procedure

To a slurry of 2-fluoro-4-formylbenzoic acid (0.531 g, 3.16 mmol) 10 mL DCM was added oxalyl chloride (0.168 mL, 1.89 mmol) and catalytic DMF (2 drops). The reaction was allowed to stir under a positive pressure of argon with a needle outlet to air. After 2 h, a quenched aliquot of the reaction (MeOH) was determined to contain no acid. The reaction was concentrated in vacuo and dried on a hood pump for 10 min to give a yellow solid, which was used without further purification.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customdried on a hood pump for 10 min
  3. customto give a yellow solid, which
  4. customwas used without further purification

Sources & evidence

ORD record
ord-119b3e7494d84a759cdca37daad85b1a
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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