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

HRID 1864945Notes

Reaction equation

HRID 1864945 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)C=O.C(Cl)(=O)C([Cl:28])=O>C(Cl)Cl>[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 chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4′-trifluoromethylbiphenyl-2-carboxylic acid (5.06 g), dimethylformamide (catalytic amount) and methylene chloride (30 mL) was added dropwise oxalyl chloride (2.43 mL) under ice-cooling. The mixture was stirred at room temperature for 100 minutes and the solvent was removed by evaporation. After azeotropic distillation with toluene, the residue was dried in vacuo to give the title compound (5.40 g).

Workup

  1. temperaturecooling
  2. customthe solvent was removed by evaporation
  3. distillationAfter azeotropic distillation with toluene
  4. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-e9c659f5058f4954a86b2b816be3cabf
Source dataset
uspto-grants-2009_12
Patent number
US07625948B2

Reaction notes

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