反应详情

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.

1. custompartitioned between 100 ml of ether and 100 ml of H2O
2. washThe organic phase was washed with 3×100 ml of H2O
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customto give a residual oil which
7. customThis solid was triturated with petroleum ether
8. customcollected on a filter
9. washwashed with petroleum ether
10. customdried overnight