Tris(1,1-dimethylethyl)phosphine → 3-(Dibenzofuran-2-yl)-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole

HRID 1747206Notes

Reaction equation

HRID 1747206 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:36]2[C:35]3[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=3[O:33][C:32]=2[CH:31]=[CH:30][C:29]=1[C:41]1[CH:42]=[CH:43][C:44]2[NH:45][C:46]3[C:51]([C:52]=2[CH:53]=1)=[CH:50][CH:49]=[CH:48][CH:47]=3.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].CCCCCC.C1(C)C=CC=CC=1>[CH:28]1[C:36]2[C:35]3[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=3[O:33][C:32]=2[CH:31]=[CH:30][C:29]=1[C:41]1[CH:42]=[CH:43][C:44]2[N:45]([C:2]3[CH:3]=[CH:4][C:5]([C:8]4[C:21]5[C:16]([C:15]([C:22]6[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=6)=[C:14]6[C:9]=4[CH:10]=[CH:11][CH:12]=[CH:13]6)=[CH:17][CH:18]=[CH:19][CH:20]=5)=[CH:6][CH:7]=3)[C:46]3[C:51]([C:52]=2[CH:53]=1)=[CH:50][CH:49]=[CH:48][CH:47]=3

Participants

8

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 221382759-(4-Bromophenyl)-10-phenylanthraceneHCID 23676156Sodium t-butoxideHCID 579976693-(Dibenzofuran-2-yl)-9H-carbazole

Product 1

HCID 866645023-(Dibenzofuran-2-yl)-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazoleYield 81.4%

Reagents, catalysts & solvents 3

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

Procedure

Into a 200-mL three-neck flask were put 1.0 g (2.6 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 0.86 g (2.6 mmol) of 3-(dibenzofuran-2-yl)-9H-carbazole, and 0.50 g (5.2 mmol) of sodium tert-butoxide. The air in the flask was replaced with nitrogen, and then, to the mixture were added 50 mL of toluene and 0.20 mL of tri(tert-butyl)phosphine (a 10 wt % hexane solution). This mixture was degassed under reduced pressure while being stirred, and then 75 mg (0.13 mmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture. This mixture was stirred at 110° C. for 2 hours under a nitrogen stream. After the stirring, this mixture was subjected to suction filtration through Celite, alumina, and Florisil. The obtained filtrate was concentrated to give a light-yellow oily substance. This oily substance was recrystallized from toluene/hexane to give 1.4 g of light-yellow powder in 80% yield. The synthesis scheme of Step 4 is shown in (a-4).

Workup

  1. customInto a 200-mL three-neck flask were put
  2. customThis mixture was degassed under reduced pressure
  3. stirringThis mixture was stirred at 110° C. for 2 hours under a nitrogen stream
  4. filtrationAfter the stirring, this mixture was subjected to suction filtration through Celite, alumina, and Florisil
  5. concentrationThe obtained filtrate was concentrated
  6. customto give a light-yellow oily substance
  7. customThis oily substance was recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-b15e93f4dda84e0ebbc876958a79b2e7
Source dataset
uspto-grants-2015_10
Patent number
US09150551B2

Reaction notes

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