p-Bromochlorobenzene → HCID 12327010, compound

HRID 430891Notes

Reaction equation

HRID 430891 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[C:9](=[NH:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=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:16]1([C:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:22][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 3

HCID 7806p-BromochlorobenzeneHCID 136809Benzophenone imineHCID 23676156Sodium t-butoxide

Product 1

HCID 12327010HCID 12327010, compoundYield 76%

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), bis(2-(diphenylphosphino)phenyl)ether [DPE-phos] (8.2 mg, 0.015 mmol) and 4-bromochlorobenzene (191 mg, 1.0 mmol), capped with a rubber septum, evacuated, and refilled with argon. Benzophenone imine (190 mg, 1.05 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 1 hour 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 solid (221 mg, 76%) 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 1 hour 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-22bc5312351b438f9c68e516fa00c9ad
Source dataset
uspto-grants-2001_11
Patent number
US06323366B1

Reaction notes

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