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

HRID 2177556Notes

Reaction equation

HRID 2177556 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-833f2f205ba9447c98e4b5c052c046e2
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

Loading…