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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the product of Step C (4.01 g, 15.4 mmol) in anhydrous benzene (40 mL) was added dropwise thionyl chloride (3.7 g, 30.8 mmol). The mixture was stirred 80° C. overnight. The mixture was cooled to rt, washed with saturated aqueous sodium bicarbonate solution, water and brine, and dried over magnesium sulfate, and concentrated to dryness to give the title compound as a colorless oil. The mixture was cooled to rt washed with saturated aqueous sodium bicarbonate solution, water and brine dried over magnesium sulfate concentrated to dryness

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

Procedure: To a solution of the product from Step B (5.5 g, 18.7 mmol) in diethyl ether (20 ml) was carefully added lithium aluminum hydride (0.8 g, 18.7 mmol). The mixture was stirred at room temperature for 16 h. Saturated aqueous ammonium chloride solution was added dropwise until no hydrogen gas was being generated. A few more drops of saturated aqueous ammonium chloride solution were added and the mixture was stirred at room temperature for 30 min and filtered. The filtrated was dried over magnesium sulfate and concentrated to dryness to give the title compound as a colorless oil. the mixture was stirred at room temperature for 30 min filtered The filtrated was dried over magnesium sulfate concentrated to dryness