Boron tribromide → N-Methylsalicylamide

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Reaction Steps

To a solution of N-Cyclobutyl-5-(2,6-dimethyl-4-nitro-phenoxy)-2-methoxy-N-methyl-benzamide (1.65 grams, 4.3 mmol) in methylene chloride (35 mL) at room temperature was added slowly boron tribromide (1M in methylene chloride, 8.6 mL, 8.6 mmol). The resulting mixture was stirred at room temperature for 4 hours, and quenched by pouring into ice water (100 mL), stirred for 1 hour at room temperature, then extracted with methylene chloride (3 times 30 mL). The combined organic extracts were washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered, and concentrated to give 2-hydroxy-N-methyl benzamide as a brown solid which was subjected directly to hydrogenation without further purification. 1H NMR (400 MHz, CDCl3) δ9.43 (s, 1H), 8.00 (s, 2H), 6.97-6.93 (d+dd, 2H), 6.42 (d, 1H), 4.44 (m, 1H), 2.96 (s, 3H), 2.22 (s, 6H), 2.19-2.14 (m, 2H), 1.87-1.55 (m, 4H). MS (APCI+) Calc: 370.2, Found: 371.2 (M+1).

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