Water → alpha-Resorcylic acid, 4-chloro-

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Reaction Steps

Tribromoborane (318 μL, 3.29 mmol) was added dropwise to a solution of ethyl 4-chloro-3,5-dimethoxybenzoate (2) (115 mg, 0.470 mmol) in DCM (1.5 mL) at 0° C. and the mixture was stirred at the same temperature for 4 h. The reaction mixture was allowed to warm to RT and then poured cautiously in to iced water (5 mL). The mixture was extracted with EtOAc (3×5 mL), and the combined organic extracts were washed with brine (2×5 mL), dried over MgSO4 and evaporated in vacuo to give 4-chloro-3,5-dihydroxybenzoic acid (3) (72 mg, 78%) as a brown solid: m/z 187 [M−H]− (ES−).

Provenance & Evidence