Water → 1-Iodo-3,4-methylenedioxybenzene

HRID 1165467Notes

Reaction equation

HRID 1165467 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-0b38c4b8f47d46ad96d52142dee567e5
Source dataset
uspto-grants-1990_03
Patent number
US04910198

Reaction notes

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