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

HRID 1095016노트

반응식

HRID 1095016 반응식
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

참가 물질

8

반응물 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)

생성물 1

HCID 59306584HCID 59306584, 화합물수율 42%

시약·촉매·용매 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 1140Toluene용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a13ebbd431314e5589f76e351949b17a
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08134147B2

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