Reacción #64456

Ecuación de reacción

4-bromomethyl-2'-cyanobiphenyl

lithium azide

→

title compound

Rendimiento 61.0%

4-Azidomethyl-2'-cyanobiphenyl

Rendimiento 61.0%

Disolventes

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropartitioned between 100 ml of ether and 100 ml of H2O
2. 2
   LavadoThe organic phase was washed with 3×100 ml of H2O
3. 3
   Secadodried (MgSO4)
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   Otroto give a residual oil which
7. 7
   OtroThis solid was triturated with petroleum ether
8. 8
   Otrocollected on a filter
9. 9
   Lavadowashed with petroleum ether
10. 10
    Otrodried overnight

Procedimiento

A mixture of 1.97 g (725 mole) of 4-bromomethyl-2'-cyanobiphenyl (EP 253,310), 445 mg (9.1 mmole) of lithium azide and 5 ml of dry DMSO was stirred at room temperature under nitrogen for one hour and then partitioned between 100 ml of ether and 100 ml of H2O. The organic phase was washed with 3×100 ml of H2O, then dried (MgSO4), filtered, and concentrated in vacuo to give a residual oil which solidified on standing. This solid was triturated with petroleum ether, collected on a filter, washed with petroleum ether and dried overnight to yield 1.15 g (61%) of the title compound as white crystals, mp 69°-70° C.; mass spectrum (EI) m/e 234 (M+). TLC in 4:1 hexane-EtOAc showed only minor impurities and the material was of sufficient purity to use in the next step.

Fuente