Water → (6-Bromo-3-fluoropyridin-2-yl)methanol

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Reaction Steps

6-bromo-3-fluoro-2-methylpyridine 1-oxide (2.89 g, 14.02 mmol, 1 eq.) was dissolved in neat TFAA (10 ml) and stirred 30 min at room temperature and refluxed for 2 hrs. The solvent was evaporated and the residue diluted with DCM and basified with sat. aqueous Na2CO3. The organic layers was separated and washed with sat. aqueous Na2CO3, dried with MgSO4 and concentrated. The crude was dissolved in THF and MeOH (1 ml) was added followed by K2CO3 (4.8 g, 35.07 mmol, 2.5 eq.). After 30 min of stirring, water was added and the reaction was extracted with EtOAc. The organic layers were combined, dried over MgSO4 and concentrated. (6-bromo-3-fluoropyridin-2-yl)methanol (2.54 g, 79% yield) was obtained as a yellow solid.

Provenance & Evidence