Reaktion #48314

Reaktionsgleichung

water

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

toluene

→

6-bromo-2,2-dimethyl-1,2-dihydroquinoline

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction vessel was sealed
2. 2
   Temperaturthe resulting mixture was heated to 90 deg C
3. 3
   Sonstigethe mixture was transferred to a separatory funnel
4. 4
   WaschenThe aqueous layer was washed 1× with EtOAc and 3× with DCM
5. 5
   Trocknendried with MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe crude oil was purified with an MPLC (100% DCM to 10% (91/10/1 DCM:MeOH:NH4OH))
9. 9
   Sonstigeto provide the product

Vorschrift

To a solution of 4-bromo-N-(2-methylbut-3-yn-2-yl)benzenamine (3.30 g, 14 mmol) in toluene (14 ml, 14 mmol) was added copper(I) chloride (0.300 g, 3.0 mmol) in one portion. The reaction vessel was sealed and the resulting mixture was heated to 90 deg C. After stirring overnight, the mixture was transferred to a separatory funnel containing water and EtOAc. The aqueous layer was washed 1× with EtOAc and 3× with DCM. The organic layers were combined, dried with MgSO4, filtered and concentrated. The crude oil was purified with an MPLC (100% DCM to 10% (91/10/1 DCM:MeOH:NH4OH)) to provide the product. MS m/z: 238.

Quelle