(5-fluoro-2-iodo-3-methylphenyl)methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-fluoro-2-iodo-3-methyl-benzoic acid methyl ester (11.2 g) in dichloromethane (80 mL) was added dropwise over 25 minutes diisobutyl aluminium hydride (113 mL, 1.02 mol/L hexane solution) at −78° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was added dropwise methanol (10 mL) at the same temperature, and the mixture was stirred for 10 minutes. To the reaction mixture was added a saturated potassium sodium tartrate tetrahydrate aqueous solution (300 mL) under ice-cooling, and the mixture was stirred for 30 minutes. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was washed with hexane to give (5-fluoro-2-iodo-3-methyl-phenyl)methanol (7.15 g). To a suspension of the obtained compound (7.15 g) in chloroform (53 mL) and acetone (5.2 mL) was added manganese dioxide, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=0-15%) to give the title compound (3.54 g). the mixture was stirred for 10 minutes cooling the mixture was stirred for 30 minutes The reaction mixture was extracted with ethyl acetate The organic layer was washed with brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was washed with hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-fluoro-2-iodo-3-methyl-benzoic acid methyl ester (11.2 g) in dichloromethane (80 mL) was added dropwise over 25 minutes diisobutyl aluminium hydride (113 mL, 1.02 mol/L hexane solution) at −78° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was added dropwise methanol (10 mL) at the same temperature, and the mixture was stirred for 10 minutes. To the reaction mixture was added a saturated potassium sodium tartrate tetrahydrate aqueous solution (300 mL) under ice-cooling, and the mixture was stirred for 30 minutes. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was washed with hexane to give (5-fluoro-2-iodo-3-methyl-phenyl)methanol (7.15 g). To a suspension of the obtained compound (7.15 g) in chloroform (53 mL) and acetone (5.2 mL) was added manganese dioxide, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=0-15%) to give the title compound (3.54 g). the mixture was stirred for 10 minutes cooling the mixture was stirred for 30 minutes The reaction mixture was extracted with ethyl acetate The organic layer was washed with brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was washed with hexane