Aniline → N-phenyltriphenylen-2-amine

HRID 2091441ノート

反応式

HRID 2091441 の反応式
C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.Br[C:15]1[CH:32]=[CH:31][C:30]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=1.CC(C)([O-])C.[Na+].[NH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:40]1([NH:39][C:15]2[CH:32]=[CH:31][C:30]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]=3[CH:16]=2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

参加物

8

反応物 4

HCID 6115AnilineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 183811742-BromotriphenyleneHCID 23676156Sodium t-butoxide

生成物 1

HCID 58362099N-phenyltriphenylen-2-amine収率 38.5%

試薬・触媒・溶媒 3

HCID 1140Toluene触媒HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

実験手順

Palladium acetate (0.01 g, 0.06 mmol) and 1.0 M tri(t-butyl)phosphine solution in toluene (0.02 mL, 0.02 mmol) were added to a three-neck flask under nitrogen. 100 mL of toluene was then added. The solution was stirred under nitrogen until the color disappeared. To the solution was added 2-bromotriphenylene (2 g, 6.5 mmol), sodium tert-butoxide (0.94 g, 9.8 mmol), and aniline (1.8 g, 20 mmol) in sequence. The mixture was then heated up to reflux overnight. After cooled to room temperature, the mixture was filtered through a celite bed and washed thoroughly with dichloromethane. The product was purified by column chromatography using 1:7 dichloromethane and hexanes as eluent. 0.8 g of desired product was obtained after purification.

後処理

  1. temperatureThe mixture was then heated up
  2. temperatureto reflux overnight
  3. filtrationthe mixture was filtered through a celite bed
  4. washwashed thoroughly with dichloromethane
  5. customThe product was purified by column chromatography

出典と根拠

ORDレコード
ord-95fb65a4c1ca4f839d00822364b06279
出典データセット
uspto-grants-2013_05
特許番号
US08440326B2

反応ノート

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