Iodine → 1-Iodo-3,4-methylenedioxybenzene

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).

1. waitAfter 45 min
2. customquenched with water
3. customThe THF was removed
4. additionthe residue treated with EtOAc (400 mL) and saturated Na2S2O3 solution (100 mL)
5. dry with materialThe organic layer was dried over MgSO4
6. custompurified by CC (silica gel, hexanes:EtOAc 1:1)

ORD record

ord-a620d992e1ad4dca97ee850328fa120a

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07470723B2