Dimethylformamide → 3-Fluoro-4-methylbenzoyl chloride

HRID 2415255Notes

Reaction equation

HRID 2415255 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](O)=[O:6].C(Cl)(=O)C([Cl:15])=O.CN(C)C=O>C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([Cl:15])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 676873-Fluoro-p-toluic acid

Product 1

HCID 27348753-Fluoro-4-methylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 3-fluoro-4-methyl-benzoic acid (Aldrich, 3.08 g, 20 mmol) in diethyl ether (30 mL), oxalyl chloride (2.85 mL, 30 mmol) was added slowly followed by a drop of N,N-dimethylformamide. The mixture was stirred at room temperature overnight and the solvent was removed under reduced pressure to give 3-fluoro-4-methyl-benzoyl chloride that was used directly for the next step.

Workup

  1. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5ce199ff6ba94302b2ad721dd3aeb883
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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