General procedure for the synthesis of 2-(hydroxymethyl)-5-bromothiazole using 5-bromothiazole-2-carboxaldehyde as starting material: a methanol (1.00 mL) solution of 5-bromothiazole-2-carboxaldehyde (0.100 g, 0.521 mmol) was slowly added dropwise to a methanol (2.0 mL) solution of sodium borohydride (0.030 g, 0.781 mmol) under stirring conditions. After the dropwise addition, the reaction mixture was allowed to stand at room temperature for 5 minutes, followed by continued stirring for 1 hour. Upon completion of the reaction, the solvent was removed by rotary evaporator under reduced pressure. The residue was dissolved and partitioned between ethyl acetate and water. After separation of the organic layer, the aqueous phase was further extracted with ethyl acetate. All organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford 2-(hydroxymethyl)-5-bromothiazole (0.067 g, 66% yield) as a dark-colored oil.LCMS analysis showed the [M + H]+ peak at 195.9.
