Benzene, 1-chloro-4-fluoro- → HCID 21195967, compound

Participants

Reaction Steps

Under an argon atmosphere 2-hydroxymethyl-1-[3-(1-tritylpiperidin-3-yl)propyl]-1H-indole (2.89 g, 5,61 mmol) was dissolved in about 11.2 ml of N,N-dimethylformamide. The resulting solution was then placed in an ice bath and sodium hydride (0.247 g of a 60% suspension in mineral oil, 6.18 mmol) was added and the resulting mixture was stirred at room temperature for about 60 minutes. To the reaction mixture 1-chloro-4-fluorobenzene (0.658 ml, 0.807 g, 6.18 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was then heated to 80° C. and maintained at this temperature for about eight hours. The reaction mixture was then cooled to room temperature and stirred at this temperature overnight. Another half equivalence of sodium hydride was added and the reaction mixture was stirred at room temperature overnight again. Another half equivalence of 1-chloro-4-fluorobenzene was added and the reaction mixture was heated to 80° C.

Provenance & Evidence