Diisobutylaluminum hydride → (2,6-Dichloro-5-fluoropyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2,6-dichloro-5-fluoro-3-pyridinecarboxylate (3 g, 13.39 mmol) in DCM (12 ml) at 0° C. under N2 was added dropwise DIBAL-H (1.5 M solution in toluene, 19.20 ml, 28.8 mmol). The reaction mixture was stirred at 0° C. for 20 h. TLC (DCM) showed starting material remaining. Then, more DIBAL-H (1.5 M solution in toluene, 10 ml) was added. The reaction was stirred at 0° C. for 20 h. The reaction mixture was diluted with MeOH and concentrated under reduced pressure. The residue was treated with 1N HCl solution and extracted 3 times with EtOAc. The combined organic phases were washed with sat. NaCl, dried over Na2SO4 and concentrated to give 1.5 g (53%) of the title compound.

Provenance & Evidence