Methyl iodide → 4-(2-fluorophenyl)-1-methyl-1H-1,2,3-triazole

Participants

Reaction Steps

Solution A was composed of 1-ethynyl-2-fluorobenzene (4.2 g, 35 mmol) and iodomethane (5.96 g, 42 mmol) in acetonitrile (94 mL) and Solution B was composed of sodium azide (2.73 g, 42 mmol) and copper(I) iodide (1.33 g, 6.99 mmol) in water (100 mL). The reaction was ran in Uniqsis FlowSyn apparatus at 150° C. at 100 psi with flow rate of 1.0 mL/min and residence time of 1.5 min for each solution A and B. The reaction flow eluent was collected in an aqueous ammonium hydroxide solution (25%) and the mixture extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 10 to 60% ethyl acetate in heptane) afforded the title compound (1.5 g, 24%) as a light yellow solid. MS: m/e=178.3 [M+H]+.

Provenance & Evidence