Reaktion #48313

Reaktionsgleichung

water

4-bromobenzenamine

water

3-chloro-3-methylbut-1-yne

→

product

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

Lösungsmittel

diethyl ether

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction mixture was transferred to a seperatory funnel
2. 2
   WaschenThe aqueous layer was washed 3× with EtOAc
3. 3
   Trocknendried with MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe crude oil was purified with by MPLC (100% DCM to 10% (91/10/1 DCM:MeOH:NH4OH))

Vorschrift

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).

Quelle