1,4-Dibromobenzene → HCID 85970010, compound

HRID 924553Notes

Reaction equation

HRID 924553 reaction equation
[CH:1]1[C:14]2[CH:13]=[C:12]([NH:15][C:16]3[C:17]4[C:22]([C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=5[CH:29]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:30][C:31]1[CH:36]=[CH:35][C:34](Br)=[CH:33][CH:32]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:30][C:31]1[CH:36]=[CH:35][C:34]([N:15]([C:12]2[C:11]3[C:6]([C:5]4[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=4[CH:13]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:16]2[C:17]3[C:22]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[CH:29]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 78041,4-DibromobenzeneHCID 13150007N-(Phenanthren-9-yl)phenanthren-9-amineHCID 23676156Sodium t-butoxide

Product 1

HCID 85970010HCID 85970010, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Diphenanthren-9-ylamine (4.50 g, 12.18 mmol), 1,4-dibromobenzene (3.02 mL, 25.12 mmol), Pd2(dba)3 (307 mg, 0.355 mmol), tris-o-tolyphosphine (0.255 mL, 0.837 mmol), sodium tert-butoxide (3.2 g, 33.49 mmol) were put in a 250 mL two-neck flask and dissolved in toluene. The solution was refluxed and stirred for 12 hours. After completion of the reaction, the solution was extracted with DI water/methylenechloride and distilled under reduced pressure to remove the solvent. The resultant was columned with a solution of n-hexane and methylenechloride (7:1). The resultant was distilled under reduced pressure and re-crystallized such that the wax compound was obtained, (2.8 g, yield: 44%).

Workup

  1. temperatureThe solution was refluxed
  2. customAfter completion of the reaction
  3. extractionthe solution was extracted with DI water/methylenechloride
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. distillationThe resultant was distilled under reduced pressure
  7. customre-crystallized such that the wax compound
  8. customwas obtained

Sources & evidence

ORD record
ord-cee3e005ea0842d68798aed38c2112c8
Source dataset
uspto-grants-2016_03
Patent number
US09281482B2

Reaction notes

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