P-Anisidine → 2-Methoxy-N-(4-methoxyphenyl)aniline

HRID 58938Notes

Reaction equation

HRID 58938 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.Br[C:11]1[CH:17]=[CH:16][C:14](N)=[CH:13][CH:12]=1.C[C:19](C)([O-:21])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:17]2[C:11]([O:21][CH3:19])=[CH:12][CH:13]=[CH:14][CH:16]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 7732P-AnisidineHCID 78074-BromoanilineHCID 23676156Sodium t-butoxide

Product 1

HCID 6152762-Methoxy-N-(4-methoxyphenyl)anilineYield 54.1%

Reagents, catalysts & solvents 3

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Anisidine (2.00 g, 16.2 mmol), 4-bromoaniline (3.34 g, 17.9 mmol), sodium tert-butoxide (2.34 g, 24.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.149 g, 0.162 mmol), and tri-tertbutylphosphine (0.053 g, 0.26 mmol) were put into a 100 mL 2-neck flask under nitrogen atmosphere, and 23 mL of anhydrous toluene was added thereto and stirred at 110° C. for 12 hours. When a reaction was completed, a reaction mixture was extracted with ethyl acetate, washed with salt water, and dried over MgSO4 to remove a solvent, followed by separation and purification using column chromatography (ethyl acetate/hexane=1/10), thereby obtaining the title compound (54%, 2.01 g) as a sticky solid.

Workup

  1. extractiona reaction mixture was extracted with ethyl acetate
  2. washwashed with salt water
  3. dry with materialdried over MgSO4
  4. customto remove a solvent
  5. customfollowed by separation and purification

Sources & evidence

ORD record
ord-573f6e8704e646f48f51aca24b9c0647
Source dataset
uspto-grants-2016_09
Patent number
US09437825B2

Reaction notes

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