Methanol → Methyl 2-chloro-5-(trifluoromethyl)benzoate

HRID 1591631Notes

Reaction equation

HRID 1591631 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.CO>ClCCl.CN(C)C=O>[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

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 6881822-Chloro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 15010065Methyl 2-chloro-5-(trifluoromethyl)benzoateYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-chloro-5-trifluoromethyl-benzoic acid (2.8 g, 12.5 mmol) in dichloromethane (50 ml) was added a solution of oxalyl chloride in dichloromethane (2 M, 7 ml, 14 mmol) followed by N,N-dimethylformamide (5 drops). After stirring for 2 hours, methanol (10 ml) was added. After stirring for 20 hours, the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (200 ml) and saturated aqueous potassium carbonate solution (100 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to provide methyl 2-chloro-5-trifluoromethyl-benzoate (2.6 g, 87% yield).

Workup

  1. stirringAfter stirring for 20 hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (200 ml) and saturated aqueous potassium carbonate solution (100 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-754b03199d8649ad9b95cce02a3793ca
Source dataset
uspto-grants-2007_11
Patent number
US07291616B2

Reaction notes

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