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

HRID 1009139

반응식

HRID 1009139 반응식
[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

참가 물질

7

반응물 3

HCID 962Water2회HCID 78074-BromoanilineHCID 706791-Butyne, 3-chloro-3-methyl-

생성물 1

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

시약·촉매·용매 3

HCID 23978Copper촉매HCID 62652Cuprous chloride촉매HCID 3283Diethyl Ether용매2회

실험 절차

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).

후처리

  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))

출처 및 근거

ORD 기록
ord-2df9bcd7cc664ae0af973b6eb19e64f1
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973047B2

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