Reacción #57547

Ecuación de reacción

3-Bromobenzenethiol

potassium carbonate

2-iodopropane

→

1-bromo-3-isopropylsulfanyl-benzene

Rendimiento 93.2%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThis was refluxed for 5 h
2. 2
   OtroReaction
3. 3
   Filtraciónfiltered through a pad of Celite
4. 4
   ConcentraciónThe organic was then concentrated in vacuo
5. 5
   FiltraciónThe organic was then re-filtered through the same celite plug
6. 6
   Concentraciónconcentrated in vacuo

Procedimiento

3-Bromobenzenethiol (1 g, 5.3 mmol) was added to acetone (25 mL). Next was added potassium carbonate (1.46 g, 10.58 mmol) and 2-iodopropane (1.17 g, 6.88 mmol). This was refluxed for 5 h. Reaction was then cooled to rt and filtered through a pad of Celite. The organic was then concentrated in vacuo and taken up in ether at which time a white precipitate crashed out. The organic was then re-filtered through the same celite plug and concentrated in vacuo to provide 1.14 g (93.17%) of 1-bromo-3-isopropylsulfanyl-benzene as an oil. 1H-NMR (methylene chloride -d2) δ 7.54 (s, 1H), 7.37-7.31 (m, 2H), 7.18 (t, J=7.9 Hz, 1H), 3.50-3.36 (m, 1H), 1.31 (d, J=6.1 Hz, 6H); LC-MS RT: 4.15, [M+H]+: 233.2.

Fuente