4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → HCID 19387386, compound

HRID 2399279Notes

Reaction equation

HRID 2399279 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([CH3:19])([CH3:18])[CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=1[N+:31]([O-:33])=[O:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:31]([C:22]1[CH:23]=[C:24]([C:27]([F:28])([F:29])[F:30])[CH:25]=[CH:26][C:21]=1[O:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([CH3:19])([CH3:18])[CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 11430Potassium CarbonateHCID 15117887HCID 15117887, compound

Product 1

HCID 19387386HCID 19387386, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2-hydroxy-5-(1,1,3,3-tetramethylbutyl)benzoate (520 mg, 0.002 mol), 4-chloro-3-nitrobenzotrifluoride (442 μL, 0.003 mol) and potassium carbonate were mixed in dimethylformamide (20 mL) at 150° C., under argon, for 16 h. The mixture was filtered, the solvent was evaporated and the residue flash chromatographed (silica gel, ethyl acetate/hexane) to yield the title compound. 1H NMR (250 MHz, (CD3)2SO) δ8.38 (d, 1H), 7.98 (d, 1H), 7.89 (dd, 1H), 7.78 (dd, 1H), 7.28 (d, 1H), 6.87 (d, 1H) 3.65 (s, 3H), 3.29 (s, 2H), 1.79 (s, 3H), 1.38 (s, 6H), 0.68 (s, 6H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated
  3. customthe residue flash chromatographed (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b1c0b238fce546feaa2e912186e05b35
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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