3-Fluoro-4-methoxybenzaldehyde is a useful reagent in the synthesis of resveratrol derivatives as potent inhibitors of lysine specific demethylase 1 (LSD1), a therapeutic target for cancer treatment and other related diseases. Also a reagent for the synthesis of substituted pyrazolyl piperidine derivatives as antiplatelet agents with antiplatelet aggregation activity in the human body.
GENERAL METHODS: A mixed solution of (3-fluoro-4-methoxyphenyl)methanol (1 mmol), N-bromosuccinimide (NBS, 1.3 eq.), potassium acetate (KOAc, 1.5 eq.), water (H2O, 1.5 mL), and dichloromethane (CH2Cl2, 0.5 mL) was placed in a 25 mL flask and magnetically stirred for 10 hours at room temperature. Upon completion of the reaction, the reaction mixture was poured into water (10 mL) and extracted with ethyl acetate (EtOAc, 3 x 10 mL). The organic phases were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to remove the solvent. The residue was purified by rapid column chromatography on silica gel, using petroleum ether (PE) or mixed solvent of petroleum ether/ethyl acetate (PE/EtOAc) as eluent to obtain the target product 3-fluoro-4-methoxybenzaldehyde. The structure of the product was confirmed by gas chromatography-mass spectrometry (GC-MS) and nuclear magnetic resonance hydrogen spectroscopy (1H NMR).
[1] Applied Organometallic Chemistry, 2016, vol. 30, # 7, p. 577 - 580
[2] Letters in Organic Chemistry, 2017, vol. 14, # 4, p. 254 - 260
[3] Molecules, 2018, vol. 23, # 8,
[4] ChemSusChem, 2017, vol. 10, # 17, p. 3497 - 3505
