1,3-Dibromobenzene → HCID 118112464, compound

HRID 924549Notes

Reaction equation

HRID 924549 reaction equation
[C:1]1([NH:7][C:8]2[C:9]3[C:14]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[CH:21]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=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:29][C:25]1[CH:24]=[C:23]([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[C:9]3[C:14]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[CH:21]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 79271,3-DibromobenzeneHCID 9943327N-Phenyl-9-aminophenanthreneHCID 23676156Sodium t-butoxide

Product 1

HCID 118112464HCID 118112464, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

N-phenylphenanthren-9-amine (4.51 g, 16.74 mmol), 1,3-dibromobenzene (6.05 mL, 50.23 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, (2.9 g, yield: 41%).

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-1a1d5e57fcb84509bffaf3738c86c476
Source dataset
uspto-grants-2016_03
Patent number
US09281482B2

Reaction notes

Loading…