4,4'-Dibromobiphenyl → HCID 66797677, compound

HRID 2275960Notes

Reaction equation

HRID 2275960 reaction equation
[CH3:1][C:2]1([CH3:22])[C:10]2=[CH:11][C:12]3[NH:13][C:14]4[C:19]([C:20]=3[CH:21]=[C:9]2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33](Br)=[CH:32][CH:31]=2)=[CH:26][CH:25]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[CH:35]=[CH:34][C:33]([N:13]3[C:12]4[CH:11]=[C:10]5[C:2]([CH3:22])([CH3:1])[C:3]6[C:8]([C:9]5=[CH:21][C:20]=4[C:19]4[C:14]3=[CH:15][CH:16]=[CH:17][CH:18]=4)=[CH:7][CH:6]=[CH:5][CH:4]=6)=[CH:32][CH:31]=2)=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 71104,4'-DibromobiphenylHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 665852047,7-Dimethyl-5,7-dihydroindeno[2,1-b]carbazole

Product 1

HCID 66797677HCID 66797677, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

20 g (70.58 mmol) of 12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]-fluorene and 33 g (105.87 mmol) of 4,4′-dibromobiphenyl are dissolved in toluene and degassed by introduction of a protective gas. 4.94 ml (4.94 mmol/1 M solution in toluene) of tri-tert-butylphosphine, 633.8 mg (2.82 mmol) of Pd(OAc)2 and 10.2 g (105.87 mmol) of NaOtBu are subsequently added. The solids are degassed in advance, the reaction mixture is subsequently degassed and then stirred under reflux for 5 h. The warm reaction solution is filtered through Alox B (activity grade 1), washed with water, dried and evaporated. Crystallisation from toluene gives 15.6 g (30.4 mmol) (43%) of the product as a white solid.

Workup

  1. customdegassed by introduction of a protective gas
  2. customThe solids are degassed in advance
  3. customthe reaction mixture is subsequently degassed
  4. temperatureunder reflux for 5 h
  5. customThe warm reaction solution
  6. filtrationis filtered through Alox B (activity grade 1)
  7. washwashed with water
  8. customdried
  9. customevaporated
  10. customCrystallisation from toluene

Sources & evidence

ORD record
ord-506b0acef17944429d9dc25a2ad15318
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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