Tris(1,1-dimethylethyl)phosphine → HCID 59306584, compound

HRID 41783Notes

Reaction equation

HRID 41783 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[NH:39][C:38]3[C:33](=[CH:34][C:35]([C:41]4[CH:59]=[CH:58][C:44]([N:45]([C:52]5[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=5)[C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=5)=[CH:43][CH:42]=4)=[CH:36][CH:37]=3)[C:32]=2[CH:31]=[C:30]([C:60]2[CH:78]=[CH:77][C:63]([N:64]([C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)[C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[CH:62][CH:61]=2)[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].CCCCCC.C1(C)C=CC=CC=1>[C:22]1([C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:8]([C:5]3[CH:4]=[CH:3][C:2]([N:39]4[C:40]5[CH:28]=[CH:29][C:30]([C:60]6[CH:61]=[CH:62][C:63]([N:64]([C:65]7[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=7)[C:71]7[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=7)=[CH:77][CH:78]=6)=[CH:31][C:32]=5[C:33]5[C:38]4=[CH:37][CH:36]=[C:35]([C:41]4[CH:42]=[CH:43][C:44]([N:45]([C:52]6[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=6)[C:46]6[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=6)=[CH:58][CH:59]=4)[CH:34]=5)=[CH:7][CH:6]=3)=[C:9]3[C:14]=2[CH:13]=[CH:12][CH:11]=[CH:10]3)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 221382759-(4-Bromophenyl)-10-phenylanthraceneHCID 23676156Sodium t-butoxideHCID 59306718N,N'-[9H-Carbazole-3,6-diyldi(4,1-phenylene)]bis(N-phenylaniline)

Product 1

HCID 59306584HCID 59306584, compoundYield 42%

Reagents, catalysts & solvents 3

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

Procedure

0.70 g (1.7 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 1.1 g (1.7 mmol) of 4,4′-(9H-carbazol-3,6-diyl)bis(N,N-diphenylaniline) (TP2C), and 0.49 g (9.0 mmol) of sodium tert-butoxide were put into a 100 mL three-neck flask. The air in the flask was replaced with nitrogen. Then, to the mixture were added 30 mL of toluene and 0.20 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, 46 mg (0.080 mmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture. This mixture was stirred at 110° C. for 3 hours under a stream of nitrogen. After the stirring, the mixture 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). The obtained filtrate was condensed to give a light yellow solid. This solid was recrystallized with toluene/hexane to give 0.70 g of a light yellow powder, which was the object of the synthesis, at a yield of 42%. A synthesis scheme of Step 2 is shown in (e-2) given below.

Workup

  1. customto be degassed while the pressure
  2. stirringThis mixture was stirred at 110° C. for 3 hours under a stream of nitrogen
  3. filtrationAfter the stirring, the mixture 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)
  4. customcondensed
  5. customto give a light yellow solid
  6. customThis solid was recrystallized with toluene/hexane

Sources & evidence

ORD record
ord-1f9e3ef310314c41b9265a2c4e94fef1
Source dataset
uspto-grants-2013_09
Patent number
US08530672B2

Reaction notes

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