(Trifluoromethyl)trimethylsilane → 1-(6-Bromopyridin-3-yl)-2,2,2-trifluoroethan-1-ol

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Reaction Steps

According to Reference Example 8-12, by use of 6-bromo-3-pyridinecarboxaldehyde (1.00 g, 5.37 mmol), (trifluoromethyl)trimethylsilane (935 μL, 6.45 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 537 μL, 0.537 mmol) and tetrahydrofuran (20 mL), the mixture was stirred and reacted at room temperature for 1 hour. Then, purification by silica gel column chromatography (chloroform/methanol=19/1) was performed to give 2-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)pyridine (Compound DD) (1.12 g, yield: 81%).

Provenance & Evidence