Methyl Salicylate → Methyl 2-(2-nitro-4-trifluoromethylphenoxy)benzoate

HRID 2399273Notes

Reaction equation

HRID 2399273 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Cl[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[N+:23]([C:14]1[CH:15]=[C:16]([C:19]([F:20])([F:21])[F:22])[CH:17]=[CH:18][C:13]=1[O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])([O-:25])=[O:24]

Participants

6

Reactant 3

HCID 4133Methyl SalicylateHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 11430Potassium Carbonate

Product 1

HCID 8565042Methyl 2-(2-nitro-4-trifluoromethylphenoxy)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of methyl salicylate (15.2 g, 0.1 mol), 4-chloro-3-nitrobenzotrifluoride (22.6 g, 0.1 mol), and potassium carbonate (8.3 g, 0.06 mol) in dimethylformamide (100 mL) was stirred under argon and heated in an oil bath to 150° C. for 70 min. The reaction mixture was diluted with ethyl acetate (300 mL), filtered, and the residue washed with ethyl acetate. The combined filtrates were evaporated, and the crude product was purified by flash chromatography (silica gel, ethyl acetate/hexane) to give the title compound as a pale yellow solid; mp 69°-70° C.

Workup

  1. filtrationfiltered
  2. washthe residue washed with ethyl acetate
  3. customThe combined filtrates were evaporated
  4. customthe crude product was purified by flash chromatography (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-826cb5f089d44b83b296d6a66c0e1201
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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