Dimethylformamide → 2-Chloro-3-(trifluoromethyl)benzoyl chloride

HRID 513218

Reaction equation

HRID 513218 reaction equation
[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CN(C=O)C.C(Cl)(=O)C([Cl:23])=O>C(Cl)Cl>[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:23])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27366772-Chloro-3-(trifluoromethyl)benzoic acid

Product 1

HCID 38276332-Chloro-3-(trifluoromethyl)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-chloro-3-(trifluoromethyl)benzoic acid (15 g, 67 mmol) and catalytic DMF (0.06 mL, 0.67 mmol) in DCM (150 mL) was added oxalyl chloride (6.8 mL, 80 mmol) dropwise. The reaction was let stir (vigorous bubbling) for 4 h and concentrated to an oily solid which became solid after overnight drying on high vacuum.

Workup

  1. custom(vigorous bubbling) for 4 h
  2. concentrationconcentrated to an oily solid which
  3. customafter overnight
  4. customdrying on high vacuum

Sources & evidence

ORD record
ord-7e8ac219a9984f6494b1041233e4e050
Source dataset
uspto-grants-2015_08
Patent number
US09102686B2

Linked notes

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