2-Fluoro-6-hydroxybenzaldehyde

Uses

Synthesis

199388-02-8

38226-10-7

Step 3: Synthesis of 2-fluoro-6-hydroxybenzaldehyde A solution of 2-fluoro-6-((tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde (6.5 g, 29.0 mmol) and p-toluenesulfonic acid (TsOH, 2 g, 11.6 mmol) in dichloromethane (DCM, 30 mL) was stirred for 5 hours at room temperature. After completion of the reaction, the mixture was diluted with dichloromethane (100 mL). The organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 100:1 to 20:1 gradient elution) to afford 2-fluoro-6-hydroxybenzaldehyde (3.0 g, 74% yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3): δ 11.49 (s, 1H), 10.29 (s, 1H), 7.46-7.52 (m, 1H), 6.79 (d, J = 8.8 Hz, 1H), 6.63-6.68 (m, 1H).

References