5-bromo-2-(oxan-4-yloxy)benzonitrile

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of tetrahydro-pyran-4-ol (3.3 g, 33.0 mmol) in DMF (60 ml) at 0° C. is added sodium hydride (1.4 g, 33.0 mmol). 5-Bromo-2-fluoro-benzonitrile (5.5 g, 27.5 mmol) in DMF (30 ml) is added dropwise at 0° C. The reaction is stirred at 45° C. for 16 h. The reaction is cooled to room temperature and quenched by pouring the reaction into water (500 ml). The precipitate is filtered and dried under vacuum; yield: 6.8 g 5-bromo-2-(tetrahydro-pyran-4-yloxy)-benzonitrile; HPLC/MS: 2.27 min, [M+H]=283. The reaction is cooled to room temperature quenched by pouring the reaction into water (500 ml) The precipitate is filtered dried under vacuum 2.27 min, [M+H]=283