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

HRID 1626240

반응식

HRID 1626240 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 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; palladium촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

The round bottom flask was heated then allow to cool to room temperature under argon. Add Pd2(dba)3 (1.39 g, 1.52 mmoles, 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 mmoles) or 2-chlorotoluene (39 mL, 332.1 mmoles), lithium amide (3.47 g, 151.1 mmol, 45 mol %), sodium t-butoxide 29.5 g, 297.7 mmoles, 90 mol %), then toluene (150 mL). Heat at 80° C. under argon overnight. Let cool to room temperature. Diluted with diethyl ether then filtered through a pad of celite. Concentrated the resulting filtrate in vacuo. Used in the next reaction without purification. Purified the resulting residue by column chromatography with hexane to give 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. temperatureHeat at 80° C. under argon overnight
  3. temperatureLet cool to room temperature
  4. filtrationthen filtered through a pad of celite
  5. concentrationConcentrated the resulting filtrate in vacuo
  6. customUsed in the next reaction
  7. customwithout purification
  8. customPurified the resulting residue by column chromatography with hexane

출처 및 근거

ORD 기록
ord-bc28434e357143fbb628c77639ce971c
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785434B2

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