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

HRID 72814

反応式

HRID 72814 の反応式
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]

参加物

10

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

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)).

後処理

  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

出典と根拠

ORDレコード
ord-6dc0c40063fa4ce2bed62a222591a84e
出典データセット
uspto-grants-2014_09
特許番号
US08828986B2

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