Chlorine → 2,6-Dichloropyridin-3-ol

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Reaction Conditions

Reaction Steps

100 g (0.77 mole) of 2-chloro-3-pyridinol is dissolved in 350 ml of dimethylformamide. In the course of 1.5 hours, 70 ml of chlorine (measured at -80°; 0.93 mole) is introduced at 0° into the stirred solution. The reaction mixture is subsequently stirred for 1.5 hours at 20° C and afterwards concentrated in a rotary evaporator (bath: 50°; 10 torr). To the residue are added 400 ml of water and 100 ml of ether. The two phases are separated, and the aqueous phase is extracted 5 times with 100 ml of ether each time. The combined ether phases are washed with water and dried. The solvent is removed in vacuo; the semisolid residue is stirred with 1.6 liters of water, and the resulting suspension is adjusted to pH 3. The suspension is heated to boiling, and after a few minutes the solution is decanted from an oily residue. The solution is purified with active charcoal, and the yellow product, obtained on cooling, is recrystallised from water; m.p. 136°-138° C; yield: 42 g;

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