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4,4'-Dibromo-2,2',3,3',5,5',6,6'-octafluoro-1,1'-biphenyl → 4-bromo-4'-[N-(9-anthracenyl)-N-phenylamino]-2,2',3,3',5,5',6,6'-octafluoro-1,1'-biphenyl

HRID 132508
Notes
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Reaction equation

HRID 132508 reaction equation
C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.Br[C:15]1[C:20]([F:21])=[C:19]([F:22])[C:18]([C:23]2[C:28]([F:29])=[C:27]([F:30])[C:26]([Br:31])=[C:25]([F:32])[C:24]=2[F:33])=[C:17]([F:34])[C:16]=1[F:35].[CH:36]1[C:49]2[C:40](=[CH:41][C:42]3[C:47]([C:48]=2[NH:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:39]=[CH:38][CH:37]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(=CC(=O)C)C1C=CC=CC=1.C(=CC(=O)C)C1C=CC=CC=1.[Pd].O>[Br:31][C:26]1[C:27]([F:30])=[C:28]([F:29])[C:23]([C:18]2[C:17]([F:34])=[C:16]([F:35])[C:15]([N:50]([C:48]3[C:49]4[C:40]([CH:41]=[C:42]5[C:47]=3[CH:46]=[CH:45][CH:44]=[CH:43]5)=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)=[C:20]([F:21])[C:19]=2[F:22])=[C:24]([F:33])[C:25]=1[F:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 826004,4'-Dibromo-2,2',3,3',5,5',6,6'-octafluoro-1,1'-biphenylHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 13777361N-Phenylanthracen-9-amineHCID 23676156Sodium t-butoxide

Product 1

HCID 597338494-bromo-4'-[N-(9-anthracenyl)-N-phenylamino]-2,2',3,3',5,5',6,6'-octafluoro-1,1'-biphenylYield 67.2%

Reagents, catalysts & solvents 3

HCID 85794205Bis(benzylidenacetone) palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent3×

Procedure

In a nitrogen flow, 160 mg (0.282 mmol) of palladium bis(benzylideneacetone) and 170 mg (0.846 mmol) of tri-tert-butylphosphine were dissolved in 40 ml of toluene and then stirred for 15 minutes at room temperature. Then, 0.58 g (1.27 mmol) of 4,4′-dibromo-2,2′,3,3′,5,5′,6,6′-octafluoro-1,1′-biphenyl dissolved in 50 ml of toluene was dropped into the mixture and it was stirred for 30 minutes. Furthermore, 0.34 g (1.27 mmol) of N-(9-anthracenyl)-N-phenylamine was dissolved in 50 ml of toluene and was then dropped therein, followed by the addition of 0.18 g (1.91 mmol) of sodium tert-butoxide. Then, the mixture was heated and stirred for about 8 hours in an oil bath heated at 120° C. After returning the reaction solution to room temperature, 50 ml of water was added thereto and the resultant solution was then separated into an aqueous layer and an organic layer. Furthermore, the aqueous layer was extracted with toluene and ethyl acetate, and was then combined with the previous organic layer and dried with magnesium sulfate. The solvent was evaporated and then the residue was purified by silicagel-column chromatography (toluene:hexane=1:2) to obtain 0.55 g of 4-bromo-4′-[N-(9-anthracenyl)-N-phenylamino]-2,2′,3,3′,5,5′,6,6′-octafluoro-1,1′-biphenyl.

Workup

  1. additionwas dropped into the mixture and it
  2. stirringwas stirred for 30 minutes
  3. additionwas then dropped
  4. temperatureThen, the mixture was heated
  5. stirringstirred for about 8 hours in an oil bath
  6. temperatureheated at 120° C
  7. customto room temperature
  8. customthe resultant solution was then separated into an aqueous layer
  9. extractionFurthermore, the aqueous layer was extracted with toluene and ethyl acetate
  10. dry with materialdried with magnesium sulfate
  11. customThe solvent was evaporated
  12. customthe residue was purified by silicagel-column chromatography (toluene:hexane=1:2)

Sources & evidence

ORD record
ord-38bfa6de6ea54e3399cdd5d3bfa62e2a
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07387845B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes