Tris(1,1-dimethylethyl)phosphine → N-[4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-N,N',N'-triphenyl-benzidine

HRID 1639482

Reaction equation

HRID 1639482 reaction equation
BrC1C=CC([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:15]4[C:20]([C:21]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)=[C:22]5[C:27]=3[CH:26]=[CH:25][CH:24]=[CH:23]5)=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:10][CH:9]=2)=CC=1.[C:34]1([NH:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]3[CH:65]=[CH:64][C:50]([N:51]([C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)[C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)=[CH:49][CH:48]=3)=[CH:43][CH:42]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C[C:67]([CH3:70])([O-])[CH3:68].[Na+].[C:72](P(C(C)(C)C)C(C)(C)C)(C)([CH3:74])[CH3:73]>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].C1(C)C=CC=CC=1>[C:11]1([C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]([C:28]3[CH:29]=[CH:30][C:31]([C:55]4[CH:56]=[CH:57][C:52]([N:51]([C:58]5[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=5)[C:50]5[CH:64]=[CH:65][C:47]([C:44]6[CH:45]=[CH:46][C:41]([N:40]([C:68]7[CH:67]=[CH:70][CH:74]=[CH:72][CH:73]=7)[C:34]7[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=7)=[CH:42][CH:43]=6)=[CH:48][CH:49]=5)=[CH:53][CH:54]=4)=[CH:32][CH:33]=3)=[C:22]3[C:27]=2[CH:26]=[CH:25][CH:24]=[CH:23]3)[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 22013295N4,N4,N4'-Triphenyl-[1,1'-biphenyl]-4,4'-diamineHCID 23676156Sodium t-butoxideHCID 588506609-(4'-Bromobiphenyl-4-yl)-10-phenylanthracene

Product 1

HCID 59221695N-[4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-N,N',N'-triphenyl-benzidineYield 50%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent2×

Procedure

Into a 50 mL three-neck flask were put 1.1 g (2.2 mmol) of 9-(4′-bromobiphenyl-4-yl)-10-phenylanthracene, 0.93 g (2.2 mmol) of N,N′,N′-triphenylbenzidine (abbreviation: DPBA), and 1.0 g (10 mmol) of sodium tert-butoxide, and the atmosphere in the flask was replaced with nitrogen. Then, 15 mL of toluene and 0.10 mL of tri(tert-butyl)phosphine (10 wt % hexane solution) were added into this mixture. After this mixture was degassed under reduced pressure while being stirred, 58 mg (0.10 mmol) of bis(dibenzylideneacetone)palladium(0) was added thereto. Then, the mixture was stirred at 90° C. for 3 hours. After the stirring, about 20 mL of toluene was added into the mixture. The mixture was subjected to suction filtration to remove the solid, the obtained filtrate was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). A solid obtained by concentration of the filtrate was recrystallized with toluene/hexane to give 0.92 g of a light yellow solid, which was the object of the synthesis, in a yield of 50%.

Workup

  1. customInto a 50 mL three-neck flask were put
  2. customAfter this mixture was degassed under reduced pressure
  3. stirringThen, the mixture was stirred at 90° C. for 3 hours
  4. filtrationThe mixture was subjected to suction filtration
  5. customto remove the solid
  6. filtrationthe obtained filtrate was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135)
  7. customA solid obtained by concentration of the filtrate
  8. customwas recrystallized with toluene/hexane

Sources & evidence

ORD record
ord-4eb7e130332245f484d617668ecff742
Source dataset
uspto-grants-2012_02
Patent number
US08110122B2

Linked notes

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