Oxalyl chloride → 4-Chloro-2-methoxy-5-(6-trifluoromethyl-pyridin-3-yl)-benzoyl chloride

HRID 448941Notes

Reaction equation

HRID 448941 reaction equation
[Cl:1][C:2]1[C:10]([C:11]2[CH:12]=[N:13][C:14]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:16]=2C#N)=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([O:23][CH3:24])[CH:3]=1.C(Cl)(=O)C([Cl:28])=O>CN(C=O)C.ClCCl>[Cl:1][C:2]1[C:10]([C:11]2[CH:12]=[N:13][C:14]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:16]=2)=[CH:9][C:5]([C:6]([Cl:28])=[O:7])=[C:4]([O:23][CH3:24])[CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 686021944-Chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-methoxy-benzoic acid

Product 1

HCID 866425784-Chloro-2-methoxy-5-(6-trifluoromethyl-pyridin-3-yl)-benzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirring dichloromethane solution (5 mL) containing 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-methoxy-benzoic acid (Step 38C or 38C.1, 436 mg, 1.2 mmol), was added 2 drops of DMF and then oxalyl chloride (128 μL, 1.5 mmol) under N2. The mixture was stirred at rt for 2 hrs and concentrated to yield 4-chloro-2-methoxy-5-(6-trifluoromethyl-pyridin-3-yl)-benzoyl chloride as a solid, which was used in the next step without further purification.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-31faa044c62f4f93882af6d97b848235
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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