Methyl 5-nitro-2-(trifluoromethoxy)phenyl carbonate → 5-Amino-2-(trifluoromethoxy)phenyl methyl carbonate

HRID 383356Notes

Reaction equation

HRID 383356 reaction equation
[C:1](=[O:19])([O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:6]=1[O:14][C:15]([F:18])([F:17])[F:16])[O:2][CH3:3]>C(OCC)(=O)C.[Pd]>[C:1](=[O:19])([O:2][CH3:3])[O:4][C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:6]=1[O:14][C:15]([F:18])([F:17])[F:16]

Participants

4

Reactant 1

HCID 59395076Methyl 5-nitro-2-(trifluoromethoxy)phenyl carbonate

Product 1

HCID 593950825-Amino-2-(trifluoromethoxy)phenyl methyl carbonateYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 5-nitro-2-(trifluoromethoxy)phenyl carbonate (120 mg, 0.43 mmol) in ethyl acetate (10 mL) was stirred in presence of 10% Pd/C (45 mg) under H2 atmosphere for 4 h. The reaction was filtered through a pad of Celite and concentrated in vacuo to provide 5-amino-2-(trifluoromethoxy)phenyl methyl carbonate (90 mg, 84% yield). 1H NMR (400.0 MHz, CDCl3) δ 7.09 (dd, J=1.1, 8.7 Hz, 1H), 6.54 (d, J=2.7 Hz, 1H), 6.51 (dd, J=2.8, 8.7 Hz, 1H), 3.91 (s, 3H), 3.80 (br s, 2H).

Workup

  1. filtrationThe reaction was filtered through a pad of Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60f9ecbb44044cc5a621a0c1217bb4ae
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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