[2-(difluoromethyl)phenyl]methanol

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

Procedure: A mixture of (2-(difluoromethyl)phenyl)methanol (100 mg, 0.632 mmol) and manganese oxide (275 mg, 3.16 mmol) in dichloromethane was stirred at room temperature for twelve hours and then at 45° C. for 1 h. The reaction was filtered through celite and concentrated, to give 2-(difluoromethyl)benzaldehyde as an oil (99 mg). 1H NMR (400 MHz, CDCl3) δ 10.2 (s, 1H), 7.94 (d, 1H), 7.81 (d, 1H), 7.70 (m, 2H), 6.93 (t, 1H). The reaction was filtered through celite and concentrated

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

Procedure: To a solution of methyl 2-(difluoromethyl)benzoate (700 mg, 3.76 mmol) in THF was added 1M lithium aluminum hydride in THF (5.64 mL, 11.3 mmol) dropwise at room temperature for 1 h. The reaction was then poured into ice water (100 mL) and diluted with ethyl acetate (200 mL) and 2N sodium hydroxide aqueous solution (100 mL). The organic phase was then separated and washed with brine (50 mL), dried over sodium sulfate and concentrated, to give (2-(difluoromethyl)phenyl)methanol as an oil (480 mg). 1H NMR (400 MHz, CDCl3) δ 7.56 (d, 1H), 7.41 (m, 3H), 6.93 (t, 1H), 4.82 (s, 2H). The organic phase was then separated washed with brine (50 mL) dried over sodium sulfate concentrated