Réaction #1563911

Équation de réaction

Na2S2O3

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

iodine monochloride

→

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

Rendement 38.0%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred until the red color
2. 2
   ExtractionIt was then extracted with CH2Cl2
3. 3
   Lavagethe organic layer was washed with water and brine
4. 4
   Autredried
5. 5
   Concentrationconcentrated
6. 6
   Autreto get the crude product which
7. 7
   Autrewas purified by column chromatography (mobile phase: petroleum/methylene chloride=1/19)

Mode opératoire

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).

Source