Pyridine → tert-butyl 3-bromo-5-[(E)-hydroxyiminomethyl]benzoate

Participants

Reaction Steps

To a solution of tert-butyl 3-bromo-5-formylbenzoate (440 mg, 1.54 mmol) in dioxane (7 mL) were added hydroxylamine hydrochloride (107 mg, 1.54 mmol) and pyridine (0.13 mL, 1.54 mol). The reaction mixture was stirred at ambient temperature. After 72 h, additional hydroxylamine hydrochloride (29 mg, 0.29 mmol) and pyridine (25 μL, 0.31 mol) were added. The mixture was stirred at ambient temperature. Ater 3 h, the mixture was concentrated. Saturated aqueous NaHCO3 was added the mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated (470 mg). MS 243 (M-ten-butyl).

Provenance & Evidence