Hydrogen Bromide → 2-Bromo-5-(phenylthio) pyridine

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Reaction Steps

2-Amino-5-(phenylthio)pyridine (16.9 g., 0.1 mole) is added to 40 ml. of 48% hydrobromic acid, cooled to 10° C in an ice bath. While maintaining a temperature of 0°, the resultant hydrobromide salt is treated with 37.5 g. of bromine dropwise. The temperature is reduced and maintained at -10° while 14.0 g. of sodium nitrite in 200 ml. of water is added dropwise. After 1 hour at 0° C, the pH of the reaction mixture is adjusted to pH7 with 30% aqueous sodium hydroxide. Following the same workup as for the 2-chloro ananlogue, there is obtained 2-bromo-5-(phenylthio) pyridine.

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