[Cl:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:11]C(=O)OC(C)(C)C.Cl.O1CCOCC1>>[Cl:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:11]To a vial containing tert-butyl 4-chlorobenzo[d][1,3]dioxol-5-ylcarbamate (307.2 mg, 1.1 mmol, 1 equiv.) was added 5.5 mL of 4N HCl in dioxane (22 mmol, 20 equiv.). The mixture was stirred at room temperature for 5.5 h, the solvent removed under vacuum, the residue dissolved in ethyl acetate, washed with saturated NaHCO3, and brine. The combined organic layers was dried over anhydrous Na2SO4, filtered and the solvent removed under to give a quantitative yield 4-chlorobenzo[d][1,3]dioxol-5-amine.
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