4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → HCID 19387388, compound

HRID 2399292Notes

Reaction equation

HRID 2399292 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:5](=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[OH:6].Cl[C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:25]([C:16]1[CH:17]=[C:18]([C:21]([F:22])([F:23])[F:24])[CH:19]=[CH:20][C:15]=1[O:6][C:5]1[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:4]=1[C:3]([O:2][CH3:1])=[O:13])([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 11430Potassium CarbonateHCID 79523Methyl 4-methoxysalicylate

Product 1

HCID 19387388HCID 19387388, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl-4-methoxysalicylate (12.0 g, 0.066 mol), 4-chloro-3-nitrobenzotrifluoride (9.75 mL, 0.066 mol) and potassium carbonate (18.16 g, 0.131 mol) were mixed in dimethylformamide, under argon, at 150° C. for 16 h. The reaction mixture was filtered and the solvents evaporated. The residue was flash chromatographed (silica gel, ethyl acetate/hexane) to yield the title compound. 1H NMR (250 MHz, CDCl3) δ8.25 (d, 1H), 8.04 (d, 1H), 7.65 (dd, 1H), 6.91 (dd, 1H), 6.81 (d, 1H), 6.70 (d, 1H), 3.88 (s, 3H), 3.70 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvents evaporated
  3. customchromatographed (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a62e02c1a43d4a2496b17488bf74ea56
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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