Benzene, 1-fluoro-4-(4-nitrophenoxy)- → Benzenamine, 4-(4-fluorophenoxy)-

HRID 526758

Reaction equation

HRID 526758 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 142780Benzene, 1-fluoro-4-(4-nitrophenoxy)-HCID 178418361HCID 178418361, compound

Product 1

HCID 147633Benzenamine, 4-(4-fluorophenoxy)-Yield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-fluoro-4-(4-nitrophenoxy)benzene (6.4 g, 27.44 mmol, 1.00 equiv) and 10% palladium on carbon (1 g) catalyst in methanol (200 mL) was stirred under 1 atmosphere of hydrogen at room temperature for 4 h. The catalyst was removed by filtration and the filtrate was concentrated under vacuum to give 5.4 g (97%) of 4-(4-fluorophenoxy)benzenamine as an off-white solid. 1H-NMR (300 MHz, CDCl3): δ 6.99-6.82 (m, 6H), 6.68 (d, J=8.7 Hz, 2H), 3.63 (br, 2H) ppm.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-19b139bd4de64e1e977aee590550b812
Source dataset
uspto-grants-2016_05
Patent number
US09346761B2

Linked notes

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