4,4'-Dibromobiphenyl → n,n,n',n'-Tetrakis[3-(carbazol-9-yl)phenyl]-4,4'-biphenyldiamine

HRID 555219

反応式

HRID 555219 の反応式
[CH:1]1[C:13]2[N:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([N:27]5[C:39]6[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=6[C:33]6[C:28]5=[CH:29][CH:30]=[CH:31][CH:32]=6)[CH:22]=4)[CH:17]=[CH:18][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:41]1[CH:46]=[CH:45][C:44]([C:47]2[CH:52]=[CH:51][C:50](Br)=[CH:49][CH:48]=2)=[CH:43][CH:42]=1.[CH3:54][C:55]([CH3:58])([O-])[CH3:56].[Na+].[C:60](P)([CH3:63])([CH3:62])[CH3:61]>C1(C)C=CC=CC=1>[CH:10]1[C:11]2[N:12]([C:14]3[CH:15]=[C:16]([N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([N:27]5[C:39]6[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=6[C:33]6[C:28]5=[CH:29][CH:30]=[CH:31][CH:32]=6)[CH:22]=4)[C:41]4[CH:46]=[CH:45][C:44]([C:47]5[CH:52]=[CH:51][C:50]([N:20]([C:16]6[CH:17]=[CH:18][CH:19]=[C:14]([N:12]7[C:11]8[CH:10]=[CH:9][CH:8]=[CH:7][C:63]=8[C:60]8[C:62]7=[CH:5][CH:4]=[CH:3][CH:61]=8)[CH:15]=6)[C:21]6[CH:26]=[CH:25][CH:24]=[C:23]([N:27]7[C:28]8[CH:29]=[CH:30][CH:31]=[CH:32][C:58]=8[C:55]8[C:56]7=[CH:2][CH:1]=[CH:13][CH:54]=8)[CH:22]=6)=[CH:49][CH:48]=5)=[CH:43][CH:42]=4)[CH:17]=[CH:18][CH:19]=3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 71104,4'-DibromobiphenylHCID 123165tert-ButylphosphineHCID 20648014Bis[3-(carbazol-9-yl)phenyl]amineHCID 23676156Sodium t-butoxide

生成物 1

HCID 57578467n,n,n',n'-Tetrakis[3-(carbazol-9-yl)phenyl]-4,4'-biphenyldiamine収率 164.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

1.50 g of bis[3-(carbazol-9-yl)phenyl]amine, 374 mg of 4,4′-dibromobiphenyl, 370 mg of sodium tert-butoxide, 12 mg of palladium acetate[II], and 10 ml of anhydrous toluene were added in a flask under a nitrogen atmosphere. At an inner temperature of 80° C., 42 mg of tert-butylphosphine was added by using a syringe. After 6 hours of reaction at 80° C., 50 ml of toluene was added to extract the objective substance, followed by filtration. The filtrate was concentrated to dryness to obtain a crude product. The dried crude product was purified by column chromatography to obtain 880 mg (yield 61%) of Compound 3 as a white solid. The product was identified by 1H-NMR analysis (see FIG. 3). The following 56 hydrogen atoms were detected upon 1H-NMR (CDCl3) analysis. δ (ppm): 8.096-8.122 ppm (8H), 7.501-7.643 ppm (8H), 7.274-7.472 ppm (40H).

後処理

  1. customAfter 6 hours of reaction at 80° C.
  2. extractionto extract the objective substance
  3. filtrationfollowed by filtration
  4. concentrationThe filtrate was concentrated to dryness
  5. customto obtain a crude product
  6. customThe dried crude product
  7. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-6e22b41d671f4fbea7581f603552b35e
出典データセット
uspto-grants-2011_11
特許番号
US08053092B2

関連ノート

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