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

HRID 2399295Notes

Reaction equation

HRID 2399295 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 (7.6 g, 0.05 mol), 4-chloro-3-nitrobenzotrifluoride (7.46 ml, 0.05 mol) and potassium carbonate (4.14 g, 0.03 mol) in dimethylformamide (50 ml) was stirred under argon, in an oil bath at 150° C., for three hours. The reaction mixture was diluted with ethyl acetate and filtered. The filtrate was evaporated and the residue flash chromatographed (silica gel, ethyl acetate/hexane) to give the title compound. 1H NMR (250 MHz, CDCl3) δ8.29 (d, 1H), 8.05 (dd, 1H), 7.61 (m, 2H), 7.4 (t, 1H), 7.25 (t, 1H), 6.85 (d, 1H), 3.7 (s, 3H).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. customthe residue flash chromatographed (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-857165bd7f5d43adbc6315d6dec48c68
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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