Lithium borohydride → HCID 58542045, compound

Participants

Reaction Steps

To a mixture of 5-fluoro-2-(2-methyl-2H-1,2,4-triazol-3-yl)-benzoic acid methyl ester plus regioisomer (1.5 g, 6.38 mmol) in THF (50.0 mL) is added a solution of 2 M LiBH4 in THF (10.0 mL, 20 mmol). The reaction mixture is stirred at room temperature for 16 hours and is then quenched with 4 M HCl in dioxane to give an acidic solution and concentrated under reduced pressure. The resulting residue is diluted with 1 M aqueous NaOH (100 mL), extracted with EtOAc (10 mL×3) and the combined organic layers are dried with Na2SO4 and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel flash column chromatography with 6% MeOH in CH2Cl2 as the eluent to afford [5-fluoro-2-(2-methyl-2H-1,2,4-triazol-3-yl)-phenyl]-methanol plus regiosiomer (1.0 g, 75%).

Provenance & Evidence