反応 #1563911

反応方程式

Na2S2O3

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

iodine monochloride

→

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

収率 38.0%

溶媒

methylene chloride

反応条件

後処理

1. 1
   workup.STIRRINGstirred until the red color
2. 2
   抽出It was then extracted with CH2Cl2
3. 3
   洗浄the organic layer was washed with water and brine
4. 4
   その他dried
5. 5
   濃縮concentrated
6. 6
   その他to get the crude product which
7. 7
   その他was purified by column chromatography (mobile phase: petroleum/methylene chloride=1/19)

実験手順

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).

出典