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

HRID 2114159Notes

Reaction equation

HRID 2114159 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[F:7][C:8]([F:25])([F:24])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2C(C(O)=O)=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1.CN(C)C=O>C(Cl)Cl>[F:7][C:8]([F:24])([F:25])[C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:1]([C:2]([Cl:4])=[O:3])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:13][CH:14]=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 chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (2.43 mL) was added dropwise to a mixture of 4′-trifluoromethylbiphenyl-2-carboxylic acid (5.06 g), dimethylformamide (catakytic amount) and methylene chloride (30 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 100 minutes, and concentrated to remove the solvent. The residue was evaporated azeotropically together with toluene, and dried in vacuo to give the title compound (5.40 g).

Workup

  1. temperaturecooling
  2. concentrationconcentrated
  3. customto remove the solvent
  4. customThe residue was evaporated azeotropically together with toluene
  5. customdried in vacuo

Sources & evidence

ORD record
ord-4dffe2903d274cb19ded2ca20531e31a
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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