Hydrochloric Acid → 5-Nitro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenemethanol

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Reaction Conditions

Reaction Steps

Methyl 5-nitro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (C) (2.5 g, 8.14 mmol) was dissolved in DCM (25 mL), flushed with argon and cooled in an ice bath to 0° C. A solution of 1 M diisobutylaluminum hydride in DCM (20.5 mL, 20.35 mmol) was added dropwise so that the temperature remained below 3° C. over 2 h. The black reaction mixture was stirred at 0° C. for an additional 2 h. After this time, MeOH (3 mL) was added causing a yellow precipitate to form. 1 M aqueous HCl (50 mL) was then added and reaction was stirred for 30 min at 0° C. The layers were separated and the aqueous phase was extracted with EtOAc (3×50 mL). The combined organic phases were washed with brine and dried over anhydrous MgSO4 to produce (5-nitro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (CI) as a black oil (1.25 g, 4.48 mmol, 55% yield, purity 85%). The product was used without further purification for step 3.

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