4-Benzyloxyaniline → HCID 68839626, compound

HRID 222851Notes

Reaction equation

HRID 222851 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11]([O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(C)(C)C.[K+]>CS(C)=O>[CH2:11]([O:18][C:19]1[CH:20]=[CH:21][C:22]([NH:23][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:24][CH:25]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 228604-BenzyloxyanilineHCID 738951-Fluoro-2-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 68839626HCID 68839626, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

To 600 μL of 2-fluoro-nitrobenzene, 6 mL of DMSO are added 1.7 g of 4-(benzyloxy)aniline (1.5 equivalents) and 1.02 g of potassium tert-butanolate (1.6 equivalents). The whole is heated to 110° C. for 1 h 30. The medium is then hydrolyzed and extracted several times with ethyl acetate. The organic phases are washed with a saturated solution of sodium chloride, dried on magnesium sulfate, filtered and then concentrated under reduced pressure. A silica gel chromatography of the residue (cyclohexane/ethyl acetate: 99/1) allows 754 mg of the desired product to be isolated.

Workup

  1. extractionhydrolyzed and extracted several times with ethyl acetate
  2. washThe organic phases are washed with a saturated solution of sodium chloride
  3. customdried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto be isolated

Sources & evidence

ORD record
ord-9874b494d5f048909704cfb0800d8865
Source dataset
uspto-grants-2012_06
Patent number
US08207373B2

Reaction notes

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