3-(Trifluoromethyl)benzenethiol → 2,6-Dibromo-4-(3-trifluoromethylphenylsulphanyl)-pyridine

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Reaction Steps

1.0 g (0.0056 mol) of 3-trifluoromethylthiophenol was dissolved in 17 ml of dimethylformamide and treated with 0.64 g (0.0056 mol) of potassium tert.-butylate. The mixture was stirred at room temperature for 20 min. and then treated with 1.58 g (0.0056 mol) of 2,6-dibromo-4-nitro-pyridine. The mixture was stirred at room temperature for 3 hrs., the solvent was then removed and the residue was partitioned in water and ethyl acetate. The organic phase was washed with sat. sodium chloride solution, dried over MgSO4, filtered and, after removal of the solvent, the residue was chromatographed on silica gel with ethyl acetate/hexane 1:39. There was obtained 2.08 g (90%) of 2,6-dibromo-4-(3-trifluoromethylphenylsulphanyl)-pyridine as yellow crystals; m.p.: 68-70° C.

Provenance & Evidence