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

HRID 1009139

Reaktionsgleichung

Reaktionsgleichung von HRID 1009139
[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

Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978CopperKatalysatorHCID 62652Cuprous chlorideKatalysatorHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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))

Quellen und Nachweise

ORD-Eintrag
ord-2df9bcd7cc664ae0af973b6eb19e64f1
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973047B2

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