Dimethylformamide → 2-Chloro-3-(1-cyano-1-methylethoxy)benzoyl chloride

HRID 1800648Notes

Reaction equation

HRID 1800648 reaction equation
[Cl:1][C:2]1[C:10]([O:11][C:12]([C:15]#[N:16])([CH3:14])[CH3:13])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CN(C)C=O.C(Cl)(=O)C([Cl:25])=O>O1CCCC1>[Cl:1][C:2]1[C:10]([O:11][C:12]([C:15]#[N:16])([CH3:14])[CH3:13])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:25])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 684177462-Chloro-3-(1-cyano-1-methylethoxy)benzoic acid

Product 1

HCID 866460652-Chloro-3-(1-cyano-1-methylethoxy)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-3-(1-cyano-1-methylethoxy)benzoic acid (278 mg, 1.16 mmol) produced in Example C70(iii) in tetrahydrofuran (2.5 mL) were added N,N-dimethylformamide (25 μL) and oxalyl chloride (125 μL, 1.46 mmol), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure to give 2-chloro-3-(1-cyano-1-methylethoxy)benzoyl chloride as a pale-yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-203a031050584d679f47d1cd4566d55e
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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