Oxalyl chloride → 3-Cyano-5-fluoro-benzoic acid chloride

HRID 2216781Notes

Reaction equation

HRID 2216781 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]#[N:12])[CH:10]=1)[C:5](O)=[O:6].C(Cl)(=O)C([Cl:16])=O>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]#[N:12])[CH:10]=1)[C:5]([Cl:16])=[O:6]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 27579633-Cyano-5-fluorobenzoic acid

Product 1

HCID 219425933-Cyano-5-fluoro-benzoic acid chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Fluoro-5-cyanobenzoic acid (2.5 g, 15.14 mmol) was treated with a solution of oxalyl chloride (30 mL of 2.5 M in dichloromethane, 75 mmol) and a catalytic amount of N,N-dimethylformamide. The reaction was stirred at ambient temperature for 2.5 hours. The excess oxalyl chloride was removed in vacuo to afford 3-fluoro-5-cyanobenzoyl chloride.

Workup

  1. customThe excess oxalyl chloride was removed in vacuo

Sources & evidence

ORD record
ord-9ca2fad372ab4c0eabd3759e73c25961
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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