Methyl 2-(2-nitro-4-trifluoromethylphenoxy)benzoate → HCID 15291668, compound

HRID 2399274Notes

Reaction equation

HRID 2399274 reaction equation
[N+:1]([C:4]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:5]=1[O:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])([O-])=O>[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[CH:17][C:5]=1[O:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 1

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

Product 1

HCID 15291668HCID 15291668, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2-(2-nitro-4-trifluoromethylphenoxy)benzoate (26 g, 0.076 mol) and 10% palladium on carbon (1 g) in ethyl acetate (400 mL) was hydrogenated in a parr bottle at 55 psi for 2 h. The reaction mixture was flushed with argon, filtered through Celite® and evaporated. The crude product was purified by flash chromatography (silica gel, ethyl acetate/hexane) to give the title compound as a white solid. 1H NMR (250 MHz, CDCl3) δ7.91 (dd, 1H), 7.45-7.53 (m, 1H), 7.17-7.24 (m, 1H), 6.88-7.03 (m, 3H), 6.78 (d, 1H), 4.25 (br s, 2H), 3.84 (s, 3H).

Workup

  1. customThe reaction mixture was flushed with argon
  2. filtrationfiltered through Celite®
  3. customevaporated
  4. customThe crude product was purified by flash chromatography (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-64a5d1af34dd4cf6a162111d2732af83
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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