ChemicalBook CAS DataBase List 1-IODO-3,4-METHYLENEDIOXYBENZENE

1-IODO-3,4-METHYLENEDIOXYBENZENE synthesis

5synthesis methods

Product Name:1-IODO-3,4-METHYLENEDIOXYBENZENE
CAS Number:5876-51-7
Molecular formula:C7H5IO2
Molecular Weight:248.02

274-09-9

5876-51-7

N-iodosuccinimide (14.8 g, 66.0 mmol), 1,3-benzodioxole (6.31 mL, 55.0 mmol) and acetic acid (470 mL) were added to a 1 L flask under argon protection. The reaction mixture was stirred at room temperature for 65 hours. Upon completion of the reaction, the acetic acid was removed by distillation under reduced pressure and the residue was neutralized with saturated aqueous sodium bicarbonate solution. Subsequently, aqueous sodium thiosulfate and chloroform were added to the reaction mixture to separate the organic layer. The aqueous layer was further extracted with chloroform. All organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using hexane as eluent to afford 5-iodo-1,3-benzodioxole (11.3 g, 45.7 mmol, 83% yield) in colorless liquid form.

274-09-9
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Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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5876-51-7
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$57.00/250mg

Yield: 57%

Reaction Conditions:

in acetic acid

Steps:

37 3-Benzyl-1,5-epoxy-7,8methylenedioxy-1,2,4,5-tetrahydro-3-benzazepin oxalate
EXAMPLE 37 3-Benzyl-1,5-epoxy-7,8methylenedioxy-1,2,4,5-tetrahydro-3-benzazepin oxalate To a solution of 1,2-methylenedioxybenzene (24.4 g, 0.20M) in AcOH (30 ml) was added ICI (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 H₂ O and extracted twice with ether. The organic extracts were washed with NaHSO₃, saturated NaHCO₃, H₂ O, 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 (28.8 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⁺).