General procedure for the synthesis of (2-methyl-6-nitrophenyl)methanol from 5-methyl-2-nitrobenzoic acid: to a solution of 5-methyl-2-nitrobenzoic acid (1 g, 5.5 mmol) in dichloromethane (12 mL) was added pyridine (0.44 mL, 5.5 mmol) at -10 °C and protected by nitrogen (-10 °C, -10 mmol), followed by the dropwise addition of cyanuric fluoride (0.92 mL, -11 mmol). 11 mmol). The reaction mixture was stirred at the same temperature for 1 hour. After completion of the reaction, the reaction mixture was diluted with cold water (80 mL) and extracted with dichloromethane (200 mL). The aqueous layer was then back-extracted with dichloromethane (150 mL), the organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the intermediate. The intermediate was dissolved in dichloromethane (8 mL) and sodium borohydride (0.42 g, 11 mmol) was added to the solution at room temperature under nitrogen protection. Methanol (10 mL) was then added slowly and dropwise over 10 min, and the reaction was acidified with 1N sulfuric acid upon completion. The solvent was removed by concentration under reduced pressure and the residue was diluted with water (200 mL) and extracted with ethyl acetate (200 mL). The aqueous layer was then back-extracted with ethyl acetate (250 mL), the organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give (2-methyl-6-nitrophenyl)methanol as a colorless oil (0.67 g, 72% yield). The product was confirmed by 1H NMR (CDCl3): δ 2.60 (s, 3H), 4.80 (s, 2H), 7.30 (t, 1H), 7.40 (d, 1H), 7.70 (d, 1H).
