1,4-Difluoro-2-(3-fluoro-benzyloxy)-5-nitrobenzene → 2,5-Difluoro-4-(3-fluorobenzyloxy)-phenylamine

HRID 1244574Notes

Reaction equation

HRID 1244574 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([F:11])=[CH:4][C:3]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1>C(OCC)(=O)C.[Pt]>[F:11][C:5]1[CH:4]=[C:3]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[C:2]([F:1])=[CH:7][C:6]=1[NH2:8]

Participants

4

Reactant 1

HCID 219200371,4-Difluoro-2-(3-fluoro-benzyloxy)-5-nitrobenzene

Product 1

HCID 219200542,5-Difluoro-4-(3-fluorobenzyloxy)-phenylamineYield 95.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.63 g (9.3 mmol) of 1,4-difluoro-2-(3-fluoro-benzyloxy)-5-nitrobenzene in 25 ml of ethyl acetate is hydrogenated with Pt/C (5%) as the catalyst under normal pressure during 3 hours. For the working-up, the catalyst was filtered over a Dicalit layer and the solution evaporated under reduced pressure. There are obtained 2.25 g (95% of theory) of 2,5-difluoro-4-(3-fluoro-benzyloxy)-phenylamine as a brown solid; MS: m/e=253 (M)+. The crude product is engaged in the next step without further purification.

Workup

  1. filtrationthe catalyst was filtered over a Dicalit layer
  2. customthe solution evaporated under reduced pressure

Sources & evidence

ORD record
ord-7a1abb4938d74b4cb6a56086453551ac
Source dataset
uspto-grants-2006_10
Patent number
US07122562B2

Reaction notes

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