1-Iodo-3,4-methylenedioxybenzene → 1,3-Benzodioxole

Participants

Reaction Steps

284 mgs (1.12 mmol) of bis(pinacolato)diboron under anaerobic conditions in dry methanol (3 ml) in a reaction tube was treated with 2 ml of a 1 M LiOMe solution in methanol. After stirring, 22 mg (0.028 mmol) of PtCl2(PPh3)2 was added followed by 258 mg (1.04 mmol) of 1-iodo-3,4-methylenedioxybenzene and a further 2 ml of methanol. At 60° C. the reaction goes to completion to form the desired product together with 3,4-methylenedioxybenzene. In DMSO the reaction rate is significantly slower than in methanol.

Provenance & Evidence