Water → 1-Iodo-3,4-methylenedioxybenzene

HRID 1722448Notes

Reaction equation

HRID 1722448 reaction equation
[CH2:1]1[O:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2]1.[I:10]Cl.O>CC(O)=O>[CH2:1]1[O:9][C:4]2[CH:5]=[CH:6][C:7]([I:10])=[CH:8][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 92291,3-BenzodioxoleHCID 24640Iodine chloride

Product 1

HCID 1386201-Iodo-3,4-methylenedioxybenzeneYield 57%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 1,2-methylenedioxybenzene (24.4 g, 0.20M) in AcOH (30 ml) was added ICl (40 g, 0.250M) in AcOH (50 ml) at room temperature over 0.5 hour. The reaction mixture was stirred for an additional three hours, then poured into H2O and extracted twice with ether. The organic extracts were washed with NaHSO3, saturated NaHCO3, H2O, dried (MgSO4), and evaporated in vacuo. The product was distilled under vacuum at 70° C. to give 3,4-methylenedioxyiodobenzene as a pale orange liquid (28.1 g, 57% yield). NMR (CDCl3) δ 5.85 (s, 2H, O--CH2 --O), 6.50 (d, 1H, J=8 Hz, H6), 7.10 (m, 2H, J=8 Hz, J=2 Hz, H2 and H5); MS: 248 (M+).

Workup

  1. extractionextracted twice with ether
  2. washThe organic extracts were washed with NaHSO3, saturated NaHCO3, H2O
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. distillationThe product was distilled under vacuum at 70° C.

Sources & evidence

ORD record
ord-cfc4c1e237a74e6389ba937e6e442fa2
Source dataset
uspto-grants-1989_08
Patent number
US04855426

Reaction notes

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