تفاعل #1563911

معادلة التفاعل

Na2S2O3

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

iodine monochloride

→

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

المردود 38.0%

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirred until the red color
2. 2
   استخلاصIt was then extracted with CH2Cl2
3. 3
   غسيلthe organic layer was washed with water and brine
4. 4
   أخرىdried
5. 5
   تركيزconcentrated
6. 6
   أخرىto get the crude product which
7. 7
   أخرىwas purified by column chromatography (mobile phase: petroleum/methylene chloride=1/19)

الإجراء التجريبي

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).

المصدر