4,4'-Dibromobiphenyl → HCID 20650340, compound

HRID 1618826Notes

Reaction equation

HRID 1618826 reaction equation
C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[C:14]1([CH3:28])[CH:19]=[CH:18][C:17]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)=[CH:16][CH:15]=1.Br[C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][C:39]([Br:42])=[CH:38][CH:37]=2)=[CH:32][CH:31]=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].C(OCC)(=O)C>[Br:42][C:39]1[CH:40]=[CH:41][C:36]([C:33]2[CH:34]=[CH:35][C:30]([N:20]([C:21]3[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=3)[C:17]3[CH:16]=[CH:15][C:14]([CH3:28])=[CH:19][CH:18]=3)=[CH:31][CH:32]=2)=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 71104,4'-DibromobiphenylHCID 69293Benzenamine, 4-methyl-N-(4-methylphenyl)-HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxide

Product 1

HCID 20650340HCID 20650340, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of tris(dibenzylideneacetone)dipalladium (353 mg, 0.385 mmol), and tri-tert-butyl phosphine (3.11 g of a 10% solution in hexanes) was degassed in toluene (anhydrous, 50 mL) for 20 minutes. Di-p-tolylamine (3.00 g, 15.2 mmol), and 4,4′-dibromobiphenyl (4.80 g, 15.4 mmol) were added and the mixture was further degassed for 15 minutes. Sodium tert-butoxide (2.4 g, 25 mmol) was added, and mixture was further degassed for 10 minutes. The whole was heated overnight at 120° C. under argon. After cooling, the mixture was poured into DCM, and solids were filtered off. Filtrate was washed with water and brine. The organic layer was collected and dried over sodium sulfate, then loaded onto silica gel. A flash column (gradient of 2-20% ethyl acetate in hexanes) gave 190 mg of material (3% yield); confirmed pure by HNMR.

Workup

  1. customwas degassed in toluene (anhydrous, 50 mL) for 20 minutes
  2. customthe mixture was further degassed for 15 minutes
  3. custommixture was further degassed for 10 minutes
  4. temperatureAfter cooling
  5. additionthe mixture was poured into DCM, and solids
  6. filtrationwere filtered off
  7. washFiltrate was washed with water and brine
  8. customThe organic layer was collected
  9. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-980120f058804222bc174cd9a309d273
Source dataset
uspto-grants-2014_07
Patent number
US08771845B2

Reaction notes

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