Oxalyl chloride → 4-Cyano-2-fluorobenzoyl chloride
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
Product 1
Reagents, catalysts & solvents 2
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.