Water → 4-bromo-N-(2-methylbut-3-yn-2-yl)benzenamine

HRID 20035

反応式

HRID 20035 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.O.Cl[C:11]([CH3:15])([CH3:14])[C:12]#[CH:13]>[Cu].[Cu]Cl.C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:11]([CH3:15])([C:12]#[CH:13])[CH3:14])=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 962Water2 回HCID 78074-BromoanilineHCID 706791-Butyne, 3-chloro-3-methyl-

生成物 1

HCID 200822714-bromo-N-(2-methylbut-3-yn-2-yl)benzenamine

試薬・触媒・溶媒 3

HCID 23978Copper触媒HCID 62652Cuprous chloride触媒HCID 3283Diethyl Ether溶媒2 回

実験手順

To a solution of 4-bromobenzenamine (4.0 g, 23 mmol), TEA (4.3 ml, 31 mmol), 2.0 ml of water, copper (0.058 g, 0.91 mmol) and copper(I) chloride (0.058 g, 0.59 mmol) in diethyl ether (9.8 ml, 20 mmol) was added 3-chloro-3-methylbut-1-yne (2.0 g, 20 mmol), dropwise. After stirring overnight, the reaction mixture was transferred to a seperatory funnel containing water and diethyl ether. The aqueous layer was washed 3× with EtOAc. The organic layers were combined, dried with MgSO4, filtered and concentrated. The crude oil was purified with by MPLC (100% DCM to 10% (91/10/1 DCM:MeOH:NH4OH)) to provide the product as an oil. MS m/z: 240 (M+2).

後処理

  1. customthe reaction mixture was transferred to a seperatory funnel
  2. washThe aqueous layer was washed 3× with EtOAc
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude oil was purified with by MPLC (100% DCM to 10% (91/10/1 DCM:MeOH:NH4OH))

出典と根拠

ORDレコード
ord-84f384e1b4ca4b4897235a5af4920794
出典データセット
uspto-grants-2010_06
特許番号
US07745484B2

関連ノート

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