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

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.

1. temperaturerefluxed for 2 hrs
2. customThe solvent was evaporated
3. additionthe residue diluted with DCM and basified with sat. aqueous Na2CO3
4. customThe organic layers was separated
5. washwashed with sat. aqueous Na2CO3
6. dry with materialdried with MgSO4
7. concentrationconcentrated
8. dissolutionThe crude was dissolved in THF
9. additionMeOH (1 ml) was added
10. stirringAfter 30 min of stirring
11. extractionthe reaction was extracted with EtOAc
12. dry with materialdried over MgSO4
13. concentrationconcentrated

ORD record

ord-cd47fbba0a7e4a3192525d2e486cd5a7

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466176B2