1-(4-Fluorophenoxy)-3-nitrobenzene → 3-(4-Fluorophenoxy)aniline

HRID 990547Notes

Reaction equation

HRID 990547 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([N+:13]([O-])=O)[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1>C(O)C.[Pd]>[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[NH2:13])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 235060301-(4-Fluorophenoxy)-3-nitrobenzene

Product 1

HCID 235060153-(4-Fluorophenoxy)anilineYield 91.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(4Fluorophenoxy)nitrobenzene (1.15 g, 4.93 mmol) from EX-634A was dissolved in ethanol (45 mL), and the solution was hydrogenated for 4 h in the presence of 5% palladium on charcoal. After the mixture was filtered through celite, the ethanol was removed in vacuo. The product was purified by flash column chromatography on silica gel eluting with ethyl acetate in hexane (1:10) to give 0.92 g (90%) of 3-(4-fluorophenoxy)aniline as a yellow oil, 99% pure by HPLC analysis. HRMS calcd. for C12H11FNO: 204.0824 [M+H]+, found: 204.0837.

Workup

  1. filtrationAfter the mixture was filtered through celite
  2. customthe ethanol was removed in vacuo
  3. customThe product was purified by flash column chromatography on silica gel eluting with ethyl acetate in hexane (1:10)

Sources & evidence

ORD record
ord-14aa1de564d34875bf6d64a1f1c057ce
Source dataset
uspto-grants-2002_10
Patent number
US06458852B1

Reaction notes

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