3-Hydroxy-5-nitrobenzotrifluoride → 3-aMino-5-(trifluoroMethyl)phenol

HRID 1178204Notes

Reaction equation

HRID 1178204 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:14])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-])=O>[OH-].[OH-].[Pd+2].CCOC(C)=O>[NH2:1][C:4]1[CH:5]=[C:6]([OH:14])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

4

Reactant 1

HCID 27562513-Hydroxy-5-nitrobenzotrifluoride

Product 1

HCID 144012293-aMino-5-(trifluoroMethyl)phenolYield 87.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-Nitro-5-trifluoromethyl-phenol 44 (1.6 g, 7.73 mmol) was added a catalytic amount of 20% palladium hydroxide on carbon and the reaction was stirred under a hydrogen atmosphere (balloon) over the weekend resulting in complete conversion to product by TLC (40% EtOAc:Hexanes). The reaction was filtered to give 3-Amino-5-trifluoromethyl-phenol (1.2 g, 6.76 mmol) as a brown/red oil.

Workup

  1. filtrationThe reaction was filtered

Sources & evidence

ORD record
ord-210cc58a507849b7a6a845b1c6e87e1c
Source dataset
uspto-grants-2007_10
Patent number
US07276502B2

Reaction notes

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