Dimethylformamide → 2-Chloro-3-(1-cyanocyclopropyl)benzoyl chloride

Reaction equation

[Cl:1][C:2]1[C:10]([C:11]2([C:14]#[N:15])[CH2:13][CH2:12]2)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CN(C)C=O.C(Cl)(=O)C([Cl:24])=O>O1CCCC1>[Cl:1][C:2]1[C:10]([C:11]2([C:14]#[N:15])[CH2:13][CH2:12]2)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:24])=[O:5]

Participants

Procedure

To a solution of 2-chloro-3-(1-cyanocyclopropyl)benzoic acid (16.0 g, 72.2 mmol) in tetrahydrofuran (150 mL) was added N,N-dimethylformamide (0.1 mL), and oxalyl chloride (7.2 mL, 84.0 mmol) was further added dropwise at 0° C., and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was concentrated under reduced pressure to dryness to give 2-chloro-3-(1-cyanocyclopropyl)benzoyl chloride as a pale-yellow oil.