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

HRID 408107

反応式

HRID 408107 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

A round-bottom flask was heated, and then allow to cool to room temperature under argon. To the flask were 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 (12, 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 %), then toluene (150 mL). The reaction mixture was heated at 80° C. under argon overnight, then allowed to cool to room temperature. The resulting liquid was diluted with diethyl ether, and then filtered through a pad of celite. The resulting cocnentrte was filtered in vacuo and used in the next reaction without purification. The crude material was purified by column chromatography with hexane to give the product as white crystals with a yellow tint (23.4 g, 118.6 mmol, 72% yield).

後処理

  1. temperatureA round-bottom flask was heated
  2. temperatureThe reaction mixture was heated at 80° C. under argon overnight
  3. temperatureto cool to room temperature
  4. filtrationfiltered through a pad of celite
  5. filtrationThe resulting cocnentrte was filtered in vacuo
  6. customused in the next reaction without purification
  7. customThe crude material was purified by column chromatography with hexane

出典と根拠

ORDレコード
ord-0845e1f1662e420f99af65bf52af23eb
出典データセット
uspto-grants-2014_06
特許番号
US08759336B2

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