Water → Methyl 3-amino-5-bromo-4-hydroxybenzoate

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Reaction Steps

To a solution of methyl 3-bromo-4-hydroxy-5-nitrobenzoate (2.00 g, 7.25 mmol) in N,N-dimethylformamide (36 mL) was slowly added tin(II) chloride dehydrate (5.50 g, 24.4 mmol). The mixture was stirred at ambient temperature. After 10 min, water was added, and organics were extracted using ethyl acetate (5×). Combined organics were dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→85% dichloromethane/methanol) gave the title compound (3.657 g, 50% purity). LC-MS [M]=246.1.

Provenance & Evidence