4-Aminophenol → 4-(4-Nitrophenoxy)benzenamine

HRID 1294073Notes

Reaction equation

HRID 1294073 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>CN(C=O)C>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([O:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:3])=[CH:5][CH:6]=2)=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydride

Product 1

HCID 802514-(4-Nitrophenoxy)benzenamineYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

To a mixture of NaH (60% oily, 880 mg, 22.0 mmol) in DMF (40 mL) was added a solution of 4-aminophenol (2.40 g, 22.0 mmol) in DMF (30 mL) followed by 1-fluoro-4-nitrobenzene (2.12 mL, 20.0 mmol). The mixture was stirred at 90° C. overnight. After cooling, the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 then evaporated. Sequence purification on SiO2 column chromatography gave the title compound (4.60 g, quant): MS m/e 229 (M−1).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customthen evaporated
  6. customSequence purification on SiO2 column chromatography

Sources & evidence

ORD record
ord-6d12f68aa3b149e797ce67dbd8d69613
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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