반응 #1563911

반응 방정식

Na2S2O3

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

iodine monochloride

→

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

수율 38.0%

용매

methylene chloride

반응 조건

후처리

1. 1
   workup.STIRRINGstirred until the red color
2. 2
   추출It was then extracted with CH2Cl2
3. 3
   세척the organic layer was washed with water and brine
4. 4
   기타dried
5. 5
   농축concentrated
6. 6
   기타to get the crude product which
7. 7
   기타was purified by column chromatography (mobile phase: petroleum/methylene chloride=1/19)

실험 절차

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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