Réaction #48314

Équation de réaction

water

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

toluene

→

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

Solvants

EtOAc

Conditions de réaction

Traitement

1. 1
   AutreThe reaction vessel was sealed
2. 2
   Températurethe resulting mixture was heated to 90 deg C
3. 3
   Autrethe mixture was transferred to a separatory funnel
4. 4
   LavageThe aqueous layer was washed 1× with EtOAc and 3× with DCM
5. 5
   Séchagedried with MgSO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   AutreThe crude oil was purified with an MPLC (100% DCM to 10% (91/10/1 DCM:MeOH:NH4OH))
9. 9
   Autreto provide the product

Mode opératoire

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.

Source