Iodine → 1-Iodo-3,4-methylenedioxybenzene

Participants

Reaction Steps

To a solution of 4-bromo-1,2-(methylenedioxy)benzene (5.0 g, 25.0 mmol) in THF (40 mL) cooled to −78° C. was added n-butyllithium (24 mL, 1.6 M, 37.3 mmol) and the mixture kept at −78° C. for 45 min. A solution of I2 (12.6 g, 50 mmol) in THF (40 mL) was then added. After 45 min, the reaction was allowed to warm to room temperature and quenched with water. The THF was removed and the residue treated with EtOAc (400 mL) and saturated Na2S2O3 solution (100 mL). The organic layer was dried over MgSO4 and purified by CC (silica gel, hexanes:EtOAc 1:1) to yield 4-iodo-1,2-(methylenedioxy)benzene (4.6 g, 18.5 mmol) in 74% yield: 1H NMR (CDCl3) δ 7.14-7.11 (m, 2H, Ar) 6.58(d, 1H, Ar), 5.94(s, 2H, CH2).

Provenance & Evidence