Oxalyl chloride → 4-Cyano-2-fluorobenzoyl chloride

HRID 970687Notes

Reaction equation

HRID 970687 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[C:5]([F:12])[CH:4]=1)#[N:2].C(Cl)(=O)C([Cl:16])=O>C(Cl)Cl.CN(C=O)C>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:16])=[O:8])=[C:5]([F:12])[CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 5906594-Cyano-2-fluorobenzoic acid

Product 1

HCID 223453434-Cyano-2-fluorobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-cyano-2-fluoro benzoic acid (650 mg, 3.9 mmol) in CH2Cl2 (20 mL) were added 2 drops of DMF and oxalyl chloride (0.7 mL, 7.8 mmol). The mixture was stirred at rt overnight and became a clear solution. The volatile was evaporated to dryness to give 4-cyano-2-fluoro-bezoyl chloride. To a solution of compound 6 (900 mg, 2.62 mmol) in THF (10 mL) was added a THF solution of 4-cyano-2-fluoro-bezoyl chloride. The mixture was stirred for 1 h, and concentrated. The residue was dissolved in EtOAc, washed with sat NaHCO3 and water. The organic layer was dried and evaporated to give compound 7 (1.2 g, 94% yield). MS found for C25H20ClFN4O2Si as (M+H)+: 491.1.

Workup

  1. customThe volatile was evaporated to dryness

Sources & evidence

ORD record
ord-ac9618a0430942a59ff612f5e5a00bf4
Source dataset
uspto-grants-2007_12
Patent number
US07312235B2

Reaction notes

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