Sodium borohydride → 2,4-Dibromothiazole-5-methanol

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Reaction Steps

(2,4-Dibromo-1,3-thiazol-5-yl)methanol 2,4-Dibromo-1,3-thiazole-5-carbaldehyde (1.74 g, 6.42 mmol) was dissolved in methanol (70 ml) at 0° C. Sodium borohydride (0.244 g, 6.42 mmol) was added in small portions. The ice-water bath was removed 10 minutes later and the reaction mixture was stirred at room temperature overnight. Solvent was removed and saturated ammonium chloride was added. 1.0N NaOH was added to adjust the pH to 10. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified by flash column chromatogrphy to give (2,4-dibromo-1,3-thiazol-5-yl)methanol (0.946 g, 3.47 mmol). 1H NMR (CDCl3-d) δ 2.11 (bs, 1H), 4.79(S, 2H).

Provenance & Evidence