N,N,N',N'-Tetramethylethylenediamine → Biphenyl

HRID 505943ノート

反応式

HRID 505943 の反応式
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(CCN(C)C)C.Br[CH:18]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[C:25]1([Mg]Br)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN(CCN(C)C)C.[Cl-].[NH4+]>>[CH:18]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 16992BromocycloheptaneHCID 25517Ammonium ChlorideHCID 178418255HCID 178418255、化合物HCID 178483772HCID 178483772、化合物

生成物 2

HCID 7095BiphenylHCID 297933Cycloheptylbenzene

実験手順

A mixture of PhMgBr (72 mL of 0.93-M THF solution, 67 mmol) and TMEDA (7.78 g, 67 mmol) was added to a mixture of bromocycloheptane (8.85 g, 50 mmol), FeCl3 (25 mL of 0.1-M THF solution, 5 mol %) at 0° C. in such a rate as keeping the reaction mixture in its pale yellow solution (1.36 mL/min. in the case of this run), using an injection pump. After completion of the addition of PhMgBr/TMEDA, the reaction mixture was stirred for 10 minutes at this temperature. The reaction mixture was treated with saturated aqueous ammonium chloride solution in a conventional manner and then distilled to give cycloheptylbenzene as a colorless oil (8.18 g, but 0.37 g of biphenyl was contained; isolated yield: 90%).

後処理

  1. distillationdistilled
  2. customto give

出典と根拠

ORDレコード
ord-9e46fe2b31c24f038e98f8373f0cbb9d
出典データセット
uspto-grants-2010_08
特許番号
US07781599B2

反応ノート

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