1-Bromo-2-chlorobenzene → N-(2-Chlorophenyl)-1,1-diphenylmethanimine

HRID 430890Notes

Reaction equation

HRID 430890 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][CH:19]=[CH:18][C:17]=1[Cl:22].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][CH:19]=[CH:18][C:17]=2[Cl:22])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 127541-Bromo-2-chlorobenzeneHCID 136809Benzophenone imineHCID 23676156Sodium t-butoxide

Product 1

HCID 15647246N-(2-Chlorophenyl)-1,1-diphenylmethanimineYield 71.3%

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), 2-bromochlorobenzene (191 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 2 hours and 5 minutes. The reaction mixture was cooled to room temperature and washed with saturated aqueous sodium chloride (2 mL). The organic layer was filtered through celite and concentrated in vacuo. The product was isolated as a yellow solid (208 mg, 71%) 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 2 hours and 5 minutes
  9. temperatureThe reaction mixture was cooled to room temperature
  10. washwashed with saturated aqueous sodium chloride (2 mL)
  11. filtrationThe organic layer was filtered through celite and
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01e7abfc793f479c944d99e4091487ce
Source dataset
uspto-grants-2001_11
Patent number
US06323366B1

Reaction notes

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