Aniline → N-phenyltriphenylen-2-amine

HRID 2091441노트

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HRID 2091441 반응식
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

참가 물질

8

반응물 4

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

생성물 1

HCID 58362099N-phenyltriphenylen-2-amine수율 38.5%

시약·촉매·용매 3

HCID 1140Toluene촉매HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-95fb65a4c1ca4f839d00822364b06279
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440326B2

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