2-Fluoro-3-methoxybenzaldehyde

Chemical Properties

Uses

Synthesis

693220-47-2

103438-88-6

GENERAL STEPS: To a solution of 2-fluoro-3,N-dimethoxy-N-methylbenzamide (2.30 g, 10.8 mmol) in tetrahydrofuran (THF, 20 mL) was slowly added a toluene solution of 1 M diisobutylaluminum hydride (DIBAL-H) (12 mL, 12 mmol) at -78°C. The reaction mixture was stirred at -78 °C for 3 h before an additional toluene solution of 1 M DIBAL-H (4.2 mL, 4.2 mmol) was added. Stirring was continued at -78 °C for 30 min, followed by slow warming of the reaction mixture to room temperature. Upon completion of the reaction, the reaction was carefully quenched with saturated aqueous ammonium chloride (NH4Cl) solution. The organic phase was separated and the aqueous phase was extracted with ethyl acetate (2 x 50 mL). The combined organic phases were washed sequentially with 1 N hydrochloric acid (HCl) and saturated brine. The organic phase was dried with anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with a gradient of mixed solvents of ethyl acetate (EtOAc) and hexane (0:100 to 1:1) to afford the target compound 2-fluoro-3-methoxybenzaldehyde (1.41 g, 85% yield).1H NMR (300 MHz, CDCl3): δ 10.38 (1H, s), 7.43-7.40 (1H, m) , 7.24-7.15 (2H, m), 3.95 (3H, s).

References