Tris(1,1-dimethylethyl)phosphine → 3-[4-(9H-carbazol-9-yl)phenyl]-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole

HRID 2280108Notes

Reaction equation

HRID 2280108 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:14]([C:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:16]4[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]4)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][CH:3]=1.[CH:28]1[C:40]2[N:39]([C:41]3[CH:46]=[CH:45][C:44]([C:47]4[CH:48]=[CH:49][C:50]5[NH:51][C:52]6[C:57]([C:58]=5[CH:59]=4)=[CH:56][CH:55]=[CH:54][CH:53]=6)=[CH:43][CH:42]=3)[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]=2[CH:31]=[CH:30][CH:29]=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.CCCCCC>[CH:28]1[C:40]2[N:39]([C:41]3[CH:46]=[CH:45][C:44]([C:47]4[CH:48]=[CH:49][C:50]5[N:51]([C:2]6[CH:3]=[CH:4][C:5]([C:8]7[C:21]8[C:16]([C:15]([C:22]9[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=9)=[C:14]9[C:9]=7[CH:10]=[CH:11][CH:12]=[CH:13]9)=[CH:17][CH:18]=[CH:19][CH:20]=8)=[CH:6][CH:7]=6)[C:52]6[C:57]([C:58]=5[CH:59]=4)=[CH:56][CH:55]=[CH:54][CH:53]=6)=[CH:43][CH:42]=3)[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]=2[CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 221382759-(4-Bromophenyl)-10-phenylanthraceneHCID 23676156Sodium t-butoxideHCID 593068843-(4-(9h-Carbazol-9-yl)phenyl)-9h-carbazole

Product 1

HCID 593067693-[4-(9H-carbazol-9-yl)phenyl]-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazoleYield 81%

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Procedure

1.8 g (4.5 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 1.8 g (4.5 mmol) of 3-[4-(9H-carbazol-9-yl)phenyl]-9H-carbazole (CPC), and 1.1 g (10 mmol) of sodium tert-butoxide were put into a 200 mL three-neck flask. The air in the flask was replaced with nitrogen. To the mixture were added 25 mL of toluene and 0.10 mL of tri(tert-butyl)phosphine (a 10 wt % hexane solution). This mixture was stirred to be degassed while the pressure was reduced. After the degassing, 58 mg (0.10 mmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture. This mixture was refluxed and then cooled to room temperature. Then, to the mixture was added about 50 mL of toluene. The mixture was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina. The obtained filtrate was condensed to give a light yellow solid. This solid was recrystallized with toluene/hexane to give 2.6 g of a light yellow powdered solid, which was the object of the synthesis, at a yield of 81%. A synthesis scheme of Step 4 is shown in (f-4) given below.

Workup

  1. customto be degassed while the pressure
  2. temperatureThis mixture was refluxed
  3. filtrationThe mixture was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina
  4. customcondensed
  5. customto give a light yellow solid
  6. customThis solid was recrystallized with toluene/hexane

Sources & evidence

ORD record
ord-57c42f5152e3443c94a9c2f94104a6ff
Source dataset
uspto-grants-2015_09
Patent number
US09136479B2

Reaction notes

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