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

HRID 1007619Notes

Reaction equation

HRID 1007619 reaction equation
B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.O(C)[Li].I[C:23]1[CH:28]=[CH:27][C:26]2[O:29][CH2:30][O:31][C:25]=2[CH:24]=1>CO>[CH2:30]1[O:31][C:25]2[CH:24]=[CH:23][CH:28]=[CH:27][C:26]=2[O:29]1

Participants

5

Reactant 3

HCID 1386201-Iodo-3,4-methylenedioxybenzeneHCID 2733548Bis(pinacolato)diboraneHCID 178419045HCID 178419045, compound

Product 1

HCID 92291,3-Benzodioxole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

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.

Workup

  1. customAt 60° C.

Sources & evidence

ORD record
ord-88b26436adc243d49b67b40e09273184
Source dataset
uspto-grants-2004_09
Patent number
US06794529B2

Reaction notes

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