4-tert-Butylphenol → 2-n-Butylamino-4-(4-t-butylphenoxy)nitrobenzene

HRID 2236972

Reaction equation

HRID 2236972 reaction equation
[CH2:1]([NH:5][C:6]1[CH:11]=[C:10](F)[CH:9]=[CH:8][C:7]=1[N+:13]([O-:15])=[O:14])[CH2:2][CH2:3][CH3:4].[C:16]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([NH:5][C:6]1[CH:11]=[C:10]([O:26][C:23]2[CH:24]=[CH:25][C:20]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:21][CH:22]=2)[CH:9]=[CH:8][C:7]=1[N+:13]([O-:15])=[O:14])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 73934-tert-ButylphenolHCID 11430Potassium CarbonateHCID 59566264N-butyl-5-fluoro-2-nitroaniline

Product 1

HCID 669774222-n-Butylamino-4-(4-t-butylphenoxy)nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-n-butylamino-4-fluoronitrobenzene (10 mmol), 4-t-butylphenol (13 mmol), solid K2CO3 (30 mmol) and DMF (30 mL) was heated with stirring at 90° C. for 10 h. The reaction was quenched by cold H2O (50 mL), and the resulting mixture was extracted with EtOAc (3×100 mL). The combined EtOAc extracts were washed with brine (2×50 mL) and dried (anhydrous Na2SO4). The solvent was removed in vacuo, and the crude products were purified by silica gel column chromatography (eluting with 10% EtOAc in hexane), giving 2-n-butylamino-4-(4-t-butylphenoxy)nitrobenzene.

Workup

  1. temperaturewas heated
  2. customThe reaction was quenched by cold H2O (50 mL)
  3. extractionthe resulting mixture was extracted with EtOAc (3×100 mL)
  4. washThe combined EtOAc extracts were washed with brine (2×50 mL)
  5. dry with materialdried (anhydrous Na2SO4)
  6. customThe solvent was removed in vacuo
  7. customthe crude products were purified by silica gel column chromatography (eluting with 10% EtOAc in hexane)

Sources & evidence

ORD record
ord-f9d7fa4474884505ba43e696690a152e
Source dataset
uspto-grants-2010_05
Patent number
US07714013B2

Linked notes

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