Tris(1,1-dimethylethyl)phosphine → HCID 59306584、化合物

HRID 2061265ノート

反応式

HRID 2061265 の反応式
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

参加物

8

反応物 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)

生成物 1

HCID 59306584HCID 59306584、化合物収率 42%

試薬・触媒・溶媒 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 1140Toluene溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2d1c9e157e42457e893424fbdd0f8cb8
出典データセット
uspto-grants-2012_10
特許番号
US08278655B2

反応ノート

読み込み中…