Réaction #1757086

Équation de réaction

chloro-ester

1-Chloroethyl-(4-methylthiophenoxy)formate

sodium iodide

→

title compound

Iodoethyl (4-methylthiophenoxy)formate

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   AutreA 50 mL, three-neck, round-bottomed flask equipped with a magnetic stir bar, a reflux condenser
2. 2
   TempératureThe reaction mixture was cooled to room temperature
3. 3
   Autreinorganic solids were removed by filtration
4. 4
   ConcentrationThe clear organic phase was concentrated
5. 5
   Autreto give a viscous-oil
6. 6
   AutreThe crude product was purified by column chromatography

Mode opératoire

A 50 mL, three-neck, round-bottomed flask equipped with a magnetic stir bar, a reflux condenser, an internal thermometer, and a nitrogen inlet was charged with chloro-ester D1 (2 g, 8 mmol) and sodium iodide (1.8 g, 12 mmol) in acetonitrile (10 mL). The resulting slurry was warmed to 50° C. for 36 hours. The reaction mixture was cooled to room temperature and inorganic solids were removed by filtration. The clear organic phase was concentrated to give a viscous-oil. The crude product was purified by column chromatography using ethyl acetate and hexane to give the title compound E3b as a viscous-oil (1 g, ˜30% yield). 1H NMR (CDCl3, 400 MHz): δ 2.31 (d, J=5.6 Hz, 3H), 2.47 (s, 3H), 6.80 (q, J=6 Hz, 1H), 7.11 (d, J=8.4 Hz, 2H), 7.24 (d, J=8.8 Hz, 2H).

Source