Oxalyl chloride → 2-Methoxy-4,6-bis(trifluoromethyl)benzoyl chloride

HRID 20835

Reaction equation

HRID 20835 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([C:16]([F:19])([F:18])[F:17])[C:4]=1[C:5](O)=[O:6].C(Cl)(=O)C([Cl:23])=O>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([C:16]([F:19])([F:18])[F:17])[C:4]=1[C:5]([Cl:23])=[O:6]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27412872-Methoxy-4,6-bis(trifluoromethyl)benzoic acid

Product 1

HCID 179993452-Methoxy-4,6-bis(trifluoromethyl)benzoyl chlorideYield 109.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(methyloxy)-4,6-bis(trifluoromethyl)benzoic acid (20.2 g; 70.14 mmol) in dry DCM (400 mL), at 0° C., was added dropwise oxalyl chloride (13.4 mL; 154.31 mmol) followed by dry DMF (5 drops). The reaction was allowed to reach room temperature. After overnight stirring the solvent was evaporated in vacuo to get the title product (23.5 g) as a yellow slurry used without further purification.

Workup

  1. customto reach room temperature
  2. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-865399f9efde4960829c7c9e0ae9bec4
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Linked notes

Loading…