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2-Bromotoluene → Benzenamine, 2-methyl-N-(2-methylphenyl)-

HRID 72814
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HRID 72814 반응식
C(P(C(C)(C)C)C1C=CC=C[C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C)(C)C.Br[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29].ClC1C=CC=CC=1C.[NH2-:38].[Li+].CC(C)([O-])C.[Na+]>C(OCC)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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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].C1(C)C=CC=CC=1>[C:12]1([CH3:7])[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=1[NH:38][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 5

HCID 72362-BromotolueneHCID 72382-ChlorotolueneHCID 24532Lithium amideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxide

생성물 1

HCID 136423Benzenamine, 2-methyl-N-(2-methylphenyl)-수율 72%

시약·촉매·용매 4

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매
HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 1140Toluene용매
HCID 3283Diethyl Ether용매

실험 절차

The round-bottom flask was heated then allow to cool to room temperature under argon. Added Pd2(dba)3 (1.39 g, 1.52 mmol, 1.0 mol %) or Pd(dba)2 (1.38 g, 2.4 mmol, 1.4 mol %), 2-(di-tert-butylphosphino)biphenyl (1.09 g, 3.65 mmol, 2.4 mol %), 2-bromotoluene (40 mL, 332.1 mmol) or 2-chlorotoluene (39 mL, 332.1 mmol), lithium amide (3.47 g, 151.1 mmol, 45 mol %), sodium t-butoxide (29.5 g, 297.7 mmol, 90 mol %), followed by toluene (150 mL). The reaction mixture was heated at 80° C. under argon overnight, then allowed to cool to room temperature. Diluted with diethyl ether then filtered through a pad of Celite. Concentrated the resulting filtrate in vacuo. Used the crude material in the next reaction without purification. (Crude material can be purified by flash chromatography with hexane which gave the product as white crystals with a yellow tint (23.4 g, 118.6 mmol, 72% yield)).

후처리

  1. temperatureThe round-bottom flask was heated
  2. temperatureThe reaction mixture was heated at 80° C. under argon overnight
  3. temperatureto cool to room temperature
  4. filtrationthen filtered through a pad of Celite
  5. concentrationConcentrated the resulting filtrate in vacuo
  6. customin the next reaction
  7. customwithout purification
  8. custom(Crude material can be purified by flash chromatography with hexane which

출처 및 근거

ORD 기록
ord-6dc0c40063fa4ce2bed62a222591a84e
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08828986B2

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