Sodium Hydroxide → 2-{[(4-Fluorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)

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Reaction Steps

4-Fluorobenzenethiol (5 g) was added to a solution of sodium hydroxide (3.14 g) in ethanol (50 ml) and the resulting solution was treated with 2-picolyl chloride, hydrochloride (6.4 g) in ethanol (25 ml) and the mixture was stirred for 6 hours at ambient temperature. The mixture was filtered, the solvent removed by evaporation and the residue was converted into the hydrochloride with ethereal HCl. Recrystallisation from ethanol-ether gave 2-(((4-fluorophenyl)thio)methyl)pyridine, hydrochloride (7 g) mp 190°-2° C. (Found: C,56.1; H, 4.4; N,5.2 C12H10FNS.HCl requires C,56.4; H,4.3; N,5.4%).

Provenance & Evidence