Dichloromethane → 4-Chloro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carbonyl chloride

HRID 1510439Notes

Reaction equation

HRID 1510439 reaction equation
[Cl:1][C:2]1[C:3]([C:17]([OH:19])=O)=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.C(Cl)(=O)C([Cl:23])=O.ClCCl>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:17]([Cl:23])=[O:19])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 671210774-Chloro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylic acid

Product 1

HCID 866520834-Chloro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carbonyl chlorideYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-chloro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylic acid (0.33 g, 1.13 mmol), oxalyl chloride (0.45 mL, 5.16 mmol) and dichloromethane (10 mL) was added a drop of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 6 hours. The volatiles were removed in vacuo to obtain 4-chloro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carbonyl chloride (0.34 g, 1.1 mmol)

Workup

  1. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-a79209b2eeb1430fa1befcb7943b2eba
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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