Hydrogen Bromide → (5-iodo-2,3-dihydro-1H-indol-2-yl)methyl acetate

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Reaction Steps

A 30% wt solution containing HBr in acetic acid (25 mL) is added to a flask containing benzyl 2-(hydroxymethyl)-5-iodo-1-indolinecarboxylate (Preparation 8, 6.03 g). All of the solids are dissolved and the solution is concentrated to give a brown solid. The crude product is taken into CH2Cl2 with a small amount of methanol and triethylamine and purified by column chromatography eluting with heptane (250 mL), 20% EtOAc in heptane (500 mL), and 40% EtOAc in heptane to give 3.92 g (84%) of the title compound as a red solid. Physical characteristics: M.p. 64-66° C.; HRMS (FAB) m/z 318.0006 (C11H12INO2+H). Anal. Found: C, 41.91; H, 3.85; N, 4.35.

Provenance & Evidence