Synthesis
General procedure for the synthesis of 2-fluoro-3-hydroxymethylpyridine using 2-fluoro-3-pyridinecarboxaldehyde as starting material: sodium borohydride (1.0 g, 26 mmol) was slowly added to a solution of 2-fluoro-3-pyridinecarboxaldehyde (1.6 mL, 16 mmol) in ethanol (14 mL), and the reaction mixture was stirred for 1 hour at room temperature. Upon completion of the reaction, water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to afford the target product 2-fluoro-3-hydroxymethylpyridine (1.3 g, 10 mmol, 63% yield) as a colorless oil.
References
[1] Patent: EP3333163, 2018, A1. Location in patent: Paragraph 1401; 1402
[2] Patent: WO2010/132999, 2010, A1. Location in patent: Page/Page column 98
[3] Patent: WO2011/48082, 2011, A1. Location in patent: Page/Page column 88
[4] Organic Letters, 2017, vol. 19, # 14, p. 3895 - 3898
