4-Bromobiphenyl → HCID 15647248, compound

HRID 1282476Notes

Reaction equation

HRID 1282476 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.BrC1C=CC=CC=1C1C=CC=CC=1.[C:27](=[NH:40])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CC(C)([O-])C.[Na+].C1(C(C2C=CC=CC=2)=C(P(C2CCCCC2)C2CCCCC2)C)C=CC=CC=1.[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:34]1([C:27]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[N:40][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

9

Reactant 6

HCID 71014-BromobiphenylHCID 163292-BromobiphenylHCID 25517Ammonium ChlorideHCID 136809Benzophenone imineHCID 12010824Cy-vBRIDPHCID 23676156Sodium t-butoxide

Product 1

HCID 15647248HCID 15647248, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Into a reactor were introduced 0.466 g (2.00 mmol) of 4-bromobiphenyl and 4 mL of toluene under a nitrogen atmosphere. The bromobiphenyl was dissolved in the solvent. To this solution were added 0.399 g (2.2 mmol) of benzophenonimine, 0.231 g (2.4 mmol) of sodium t-butoxide, 13.5 mg (3 mol % based on the amine) of palladium acetate, and 46.9 mg (6 mmol % based on the amine) of the 1,1-diphenyl-2-(dicyclohexylphosphino)propene obtained in Example 2. The resultant reaction mixture was stirred at 100° C. for 16 hours and then cooled. Saturated aqueous ammonium chloride solution was added thereto, and this mixture was extracted with toluene. The extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was purified by column chromatography to obtain 0.409 g (61%) of N-(diphenylmethylene)-4-aminobiphenyl as a yellow oily substance. The results obtained are shown in Table 20.

Workup

  1. customThe resultant reaction mixture
  2. temperaturecooled
  3. extractionthis mixture was extracted with toluene
  4. dry with materialThe extract was dried with anhydrous magnesium sulfate
  5. customThereafter, the solvent was removed under reduced pressure
  6. customThe concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-b04fa9b102414431b3e884d637b9bd38
Source dataset
uspto-grants-2002_09
Patent number
US06455720B1

Reaction notes

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