Réaction #48703

Équation de réaction

potassium carbonate

1-iodopropane

3-bromothiophenol

→

1-bromo-3-propylsulfanylbenzene

Rendement 95.0%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   TempératureReflux
2. 2
   Filtrationfilter through diatomaceous earth
3. 3
   Concentrationconcentrate
4. 4
   workup.DISSOLUTIONDissolve the residue in hexanes
5. 5
   Filtrationfilter through a silica gel plug
6. 6
   Concentrationconcentrate

Mode opératoire

Reflux a suspension of potassium carbonate (22.4 g), 1-iodopropane (10.3 mL) and 3-bromothiophenol (8.4 mL) in acetone (375 mL) for 5 hours. Cool to room temperature, filter through diatomaceous earth, and concentrate. Dissolve the residue in hexanes, filter through a silica gel plug, and concentrate to give 1-bromo-3-propylsulfanylbenzene (18 g, 95%) as an oil (GC-MS: m/z=231). Add this material (12 g) to a solution of n-butyllithium (57 mmol) in THF (50 mL) at −78° C. Stir for 45 min, add 110 N,N-dimethylformamide (8.1 mL) and warm to room temperature. Stir for 15 min, pour into water (175 mL), and extract into diethyl ether (3×200 mL). Dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography) to give the title compound (7.3 g, 92%).

Source