Oxalyl chloride → Methyl 2-chloro-5-(trifluoromethyl)benzoate

HRID 2100641Notes

Reaction equation

HRID 2100641 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:15](Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:7][C:3]=1[C:4]([O:6][CH3:15])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 6881822-Chloro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 15010065Methyl 2-chloro-5-(trifluoromethyl)benzoateYield 100.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-5-(trifluoromethyl)benzoic acid (15 g, 66.8 mmol) in methylene chloride (200 mL) was added oxalyl chloride (12.7 g, 100 mmol) drop wise followed by the addition of 5-6 drops of DMF. The reaction mixture was concentrated, the residue partitioned between methylene chloride and 5% aq. sodium carbonate. The organic layer was dried (MgSO4) and concentrated to give the title compound as a pale oil (16 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between methylene chloride and 5% aq. sodium carbonate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bea4f7d9b8614ef2b3354384d0dc7cad
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

Loading…