4-Bromoanisole → N-(4-Methoxyphenyl)-1,1-diphenylmethanimine

HRID 430887Notes

Reaction equation

HRID 430887 reaction equation
[C:1](=[NH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.CC(C)([O-])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].C1(P(C2C=CC=CC=2)C2C=CC=CC=2OC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[C:2]1([C:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:14][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 77304-BromoanisoleHCID 136809Benzophenone imineHCID 23676156Sodium t-butoxide

Product 1

HCID 288432N-(4-Methoxyphenyl)-1,1-diphenylmethanimineYield 83%

Reagents, catalysts & solvents 3

HCID 4285986Bis[2-(diphenylphosphino)phenyl] etherCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent2×

Procedure

An oven-dried test tube was charged with tris(dibenzylideneacetone)dipalladium (4.6 mg, 0.005 mmol) and bis(2-(diphenylphosphino)phenyl)ether [DPE-phos] (8.2 mg, 0.015 mmol), capped with a rubber septum, evacuated and refilled with argon. Benzophenone imine (190 mg, 1.05 mmol), 4-bromoanisole (187 mg, 1.0 mmol) and toluene (2 mL) were added via syringe. The resulting solution was stirred at rt for 5 minutes. The tube was opened and sodium tert-butoxide (135 mg, 1.4 mmol) was added. The tube was again capped with the septum, and additional toluene (2 mL) was added via syringe to wash the solid from the test tube wall into the solution. The solution was stirred at room temperature with a gentle argon purge for 5 minutes, then heated at 80° C. for 4 hours and 30 minutes. The reaction mixture was cooled to room temperature, washed with saturated aqueous sodium chloride (2 mL), and the organic layer was concentrated in vacuo. The product was isolated as a yellow oil (238 mg, 83%) by flash chromatography on silica gel using 5% ethyl acetate in hexanes as eluent.

Workup

  1. customcapped with a rubber septum
  2. customevacuated
  3. additionrefilled with argon
  4. additionwas added via syringe
  5. washto wash the solid from the test tube wall into the solution
  6. stirringThe solution was stirred at room temperature with a gentle argon
  7. custompurge for 5 minutes
  8. temperatureheated at 80° C. for 4 hours and 30 minutes
  9. temperatureThe reaction mixture was cooled to room temperature
  10. washwashed with saturated aqueous sodium chloride (2 mL)
  11. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-344d756788d446b08d7989e1e1ea1f5a
Source dataset
uspto-grants-2001_11
Patent number
US06323366B1

Reaction notes

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