Tris(1,1-dimethylethyl)phosphine → 9,10-bis(4-fluorophenyl)-2-[N-phenyl-N-(9-phenyl-9H-carbazol-3-yl)amino]anthracene

HRID 1640228Notes

Reaction equation

HRID 1640228 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:6]3[C:11]([C:12]=2[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[C:30]1([NH:36][C:37]2[CH:38]=[CH:39][C:40]3[N:41]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C:42]4[C:47]([C:48]=3[CH:49]=2)=[CH:46][CH:45]=[CH:44][CH:43]=4)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>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>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:5]2[C:6]3[C:11]([C:12]([C:16]4[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=4)=[C:13]4[C:4]=2[CH:3]=[C:2]([N:36]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:37]2[CH:38]=[CH:39][C:40]5[N:41]([C:50]6[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=6)[C:42]6[C:47]([C:48]=5[CH:49]=2)=[CH:46][CH:45]=[CH:44][CH:43]=6)[CH:15]=[CH:14]4)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 592111052-Bromo-9,10-bis(4-fluorophenyl)anthraceneHCID 59815954N,9-Diphenyl-9H-carbazol-3-amine

Product 1

HCID 592110179,10-bis(4-fluorophenyl)-2-[N-phenyl-N-(9-phenyl-9H-carbazol-3-yl)amino]anthraceneYield 63.6%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

2.0 g (4.5 mmol) of 2-bromo-9,10-bis(4-fluorophenyl)anthracene, 1.7 g (4.9 mmol) of N,9-diphenyl-9H-carbazol-3-amine (PCA), 0.13 g (0.23 mmol) of bis(dibenzylideneacetone)palladium(0), and 1.1 g (11 mmol) of sodium tert-butoxide were put into a 100 mL three-neck flask, and the atmosphere of the flask was substituted with nitrogen. Thereafter, 30 mL of toluene and 0.45 g (0.23 mmol) of tri(tert-butyl)phosphine (10% hexane solution) were added to the mixture, and this reaction mixture was stirred for 6 hours at 80° C. After the reaction was completed, the reaction solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The extracted solution was combined with the organic layer, and then dried with magnesium sulfate. After drying, this mixture was subjected to suction filtration, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (eluent: toluene), and then concentrated. The obtained solid was recrystallized with a mixed solvent of chloroform and hexane, giving 2.0 g of 9,10-bis(4-fluorophenyl)-2-[N-phenyl-N-(9-phenyl-9H-carbazol-3-yl)amino]anthracene (abbreviation: 2PCAFPA) as yellow powder in 62% yield. By nuclear magnetic resonance measurement (NMR), this compound was determined to be 9,10-bis(4-fluorophenyl)-2-[N-phenyl-N-(9-phenyl-9H-carbazol-3-yl)amino]anthracene (abbreviation: 2PCAFPA).

Workup

  1. washthe reaction solution was washed with water
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried with magnesium sulfate
  4. customAfter drying
  5. filtrationthis mixture was subjected to suction filtration
  6. concentrationthe filtrate was concentrated
  7. customThe obtained residue was purified by silica gel column chromatography (eluent: toluene)
  8. concentrationconcentrated
  9. customThe obtained solid was recrystallized with a mixed solvent of chloroform and hexane

Sources & evidence

ORD record
ord-ec90a447cb434ae3904741f7e4e4db49
Source dataset
uspto-grants-2012_02
Patent number
US08110980B2

Reaction notes

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