Реакция #1563911

Уравнение реакции

Na2S2O3

N-(benzo[d][1,3]dioxol-5-ylmethyl)acetamide

iodine monochloride

→

N-((6-iodobenzo[d][1,3]dioxol-5-yl)methyl)acetamide

Выход 38.0%

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred until the red color
2. 2
   ЭкстракцияIt was then extracted with CH2Cl2
3. 3
   Промывкаthe organic layer was washed with water and brine
4. 4
   Другоеdried
5. 5
   Концентрированиеconcentrated
6. 6
   Другоеto get the crude product which
7. 7
   Другоеwas purified by column chromatography (mobile phase: petroleum/methylene chloride=1/19)

Методика

N-(benzo[d][1,3]dioxol-5-ylmethyl)acetamide (9.24 g, 47.9 mmol) was added to 1.0 M solution of iodine monochloride in methylene chloride (80 mL). The mixture was stirred at room temperature for 2 hours, and then the mixture was poured into 10% Na2S2O3 and stirred until the red color faded. It was then extracted with CH2Cl2 and the organic layer was washed with water and brine, dried and concentrated to get the crude product which was purified by column chromatography (mobile phase: petroleum/methylene chloride=1/19) to give N-((6-iodobenzo[d][1,3]dioxol-5-yl)methyl)acetamide compound as a white solid (5.82 g, 38%). LC-MS: 320 [M+1]+. 1H-NMR (DMSO-d6): δ 1.89 (s, 3H), 4.11 (d, 2H, J=6.0 Hz), 6.04 (s, 2H), 7.07 (s, 1H), 7.37 (s, 1H), 8.28 (t, 1H, J=6.0 Hz).

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