Iodine → (6-Iodo-2H-1,3-benzodioxol-5-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,4-(methylenedioxy)benzyl alcohol (1.8 g, 12 mmol) and CF3COOAg (3.434 g, 15.5 mmol) in dry CHCl3 (55 mL) at −5° C. was added I2 (3.9 g, 15.5 mmol) in portion. The resulting yellow mixture was maintain at −5° C. for 5 min, then filtered. The filtrate was washed with 20% Na2S2O3, dried and evaporated. The crude was purified by column chromatography on silica gel (petroleum ether) to obtain (6-iodobenzo[d][1,3]dioxol-5-yl)methanol (1.8 g, 56%) as a white solid. LCMS: 279[M+1]+; 1H NMR (DMSO-d6) δ 4.31 (d, 2H, J=4.2 Hz), 5.40 (t, 1H, J=4.2 Hz), 6.03 (s, 2H), 7.03 (s, 1H), 7.34 (s, 2H).

Provenance & Evidence