General procedure for the synthesis of 2-fluoro-4-nitrobenzyl alcohol from 2-fluoro-4-nitrobenzaldehyde: To a solution of 2-fluoro-4-nitrobenzaldehyde (1.0 g, 5.92 mmol) in methanol (10 mL) was slowly added sodium borohydride (814 mg, 22 mmol). The reaction mixture was stirred at room temperature for 15 min and then concentrated by rotary evaporator. The concentrated residue was subjected to liquid-liquid partitioning with ethyl acetate (100 mL) and saturated aqueous sodium chloride solution (100 mL). The combined organic phases were washed with saturated aqueous sodium chloride solution (100 mL x 2) and dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated to give the red solid product 2-fluoro-4-nitrobenzyl alcohol (1.0 g, 99% yield).
