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Iodobenzene → 2,2'-Bis(diphenylamino)-9,9'-spirobifluorene

HRID 2236963
Notes
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Reaction equation

HRID 2236963 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]3([C:26]4[CH:25]=[C:24]([NH2:27])[CH:23]=[CH:22][C:21]=4[C:20]4[C:15]3=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:4]=2[CH:3]=1.I[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C[C:36]([CH3:39])([O-])[CH3:37].[Na+].C(P([C:50]([CH3:53])([CH3:52])C)C(C)(C)C)(C)(C)C>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[C:29]1([N:1]([C:37]2[CH:36]=[CH:39][CH:52]=[CH:50][CH:53]=2)[C:2]2[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]4([C:26]5[CH:25]=[C:24]([N:27]([C:6]6[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=6)[C:2]6[CH:14]=[CH:13][CH:12]=[CH:4][CH:3]=6)[CH:23]=[CH:22][C:21]=5[C:20]5[C:15]4=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:4]=3[CH:3]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11575IodobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 154158669,9'-Spirobi[fluorene]-2,2'-diamineHCID 23676156Sodium t-butoxide

Product 1

HCID 207338852,2'-Bis(diphenylamino)-9,9'-spirobifluorene

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 1140TolueneSolvent

Procedure

2,2′-diamino-9,9′-spirobifluorene (3.46 g, 10 mmol), iodobenzene (6.8 mL, 60 mmol), Pd(OAc)2 (0.112 g, 0.5 mmol), sodium-tert-butoxide (14.4 g, 150 mmol) and tri-tert-butylphosphine (20 mL, 0.05 M in toluene, 1.0 mmol) were mixed in a flask containing with toluene (100 mL). The mixture was refluxed overnight. The solution was quenched with water and extracted twice with chloroform. The combined organic extracts were dried over MgSO4 and concentrated by rotary evaporation. Column chromatography on silica gel (hexane/chloroform=4/1) afforded products [2,2′-Bis(diphenylamino)-9,9′-spirobifluorene, hereinafter named as 22DPSF] as a white solid (4.5 g, 70%).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customThe solution was quenched with water
  3. extractionextracted twice with chloroform
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-3e81e2c92edb4ea69c3c5b1fa0ea0688
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07714145B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes