Dimethylformamide → 4'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chloride

HRID 2392583Notes

Reaction equation

HRID 2392583 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15](O)=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.CN(C=O)C.C(Cl)(=O)C([Cl:28])=O>ClCCl>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]([Cl:28])=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 552514'-(Trifluoromethyl)(1,1'-biphenyl)-2-carboxylic acidHCID 65578Oxalyl chloride

Product 1

HCID 110660004'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chlorideYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxylic acid (2.60 g, 9.77 mmol), catalytic DMF, and anhydrous dichloromethane (30 mL) at room temperature under nitrogen was added oxalyl chloride (1.38 g, 10.9 mmol) dropwise over 15 minutes and the reaction stirred at room temperature. After 18 hours, the yellow reaction solution was concentrated in vacuo to give 2.51 g of 4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chloride as a cloudy yellow liquid which was used without further purification.

Workup

  1. concentrationthe yellow reaction solution was concentrated in vacuo

Sources & evidence

ORD record
ord-76576e793e9b4193948a16c528a4da0f
Source dataset
uspto-grants-1998_09
Patent number
US05801176

Reaction notes

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