Methanol → (4-Bromo-6-methylpyridin-2-yl)methanol

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Reaction Steps

A solution of 4-bromo-2-methyl-pyridine (735 mg, 4.14 mmol) in methanol (80 mL) and H2SO4 (20 μL) is heated to reflux. A solution of (NH4)2S2O8 (3.78 g, 16.6 mmol) in water (6.5 mL) is added dropwise to the stirred mixture. Upon completion of the addition, refluxing is continued for 2 h. The mixture is cooled and the reaction is quenched by adding 1 M aq. NaS2O3 solution. The mixture is further diluted with sat. aq. NaHCO3 solution and extracted twice with EA (2×300 mL). The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 3:2 to give (4-bromo-6-methyl-pyridin-2-yl)-methanol (156 mg) as a white solid; LC-MS: tR=0.32 min, [M+1]+=201.93.

Provenance & Evidence