Reaktion #1144660

Reaktionsgleichung

2-(2-Bromophenyl)-N-(phenylmethyl)acetamide

DMS

→

N-(2-(2-Bromophenyl)ethyl)-N-(phenylmethyl)amine

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONfollowed by addition of BH3
2. 2
   Temperaturto reflux
3. 3
   Temperaturthe mixture was cooled to room temerature
4. 4
   Sonstigequenched with excess 10% HCl
5. 5
   TemperaturThe mixture was heated
6. 6
   Temperaturto reflux for 1 hr
7. 7
   WaschenAfter washing with EtOAc
8. 8
   Extraktionextracted with EtOAc
9. 9
   WaschenThe organic phase was washed with brine
10. 10
    Trocknendried over magnesium sulfate
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated in vacuo
13. 13
    SonstigeThe residue was triturated with EtOAc
14. 14
    Sonstigeto afford a colorless solid

Vorschrift

2-(2-Bromophenyl)-N-(phenylmethyl)acetamide was dissolved THF (0.2 M), followed by addition of BH3.DMS (3 eq), and the reaction was heated to reflux with stirring. After 2 hrs, the mixture was cooled to room temerature, and quenched with excess 10% HCl. The mixture was heated to reflux for 1 hr, and then cooled to room temperature. After washing with EtOAc, the aqueous phase was made alkaline with 10% sodium carbonate, and extracted with EtOAc. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was triturated with EtOAc to afford a colorless solid. EI-MS m/z 290/292 (M+H)+

Quelle