Reacción #1273118

Ecuación de reacción

hexane

Tri-n-butyltin chloride

benzo[1,2-b:4,5-b′]dithiophene

n-butyllithium

→

2,6-bis(tri-n-butylstannyl)-benzo[1,2-b:4,5-b′]dithiophene

Rendimiento 42.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawarmed to −20° C. for 30 minutes
2. 2
   workup.STIRRINGthe reaction mixture was stirred at −20° C. for 30 minutes
3. 3
   Temperaturato warm to room temperature
4. 4
   workup.WAITAfter 16 hours
5. 5
   Lavadothe reaction was successively washed with water and brine
6. 6
   Secadodried (MgSO4)
7. 7
   Concentraciónconcentrated
8. 8
   Otropurified by flash chromatography (100% hexanes)

Procedimiento

To a stirred solution of benzo[1,2-b:4,5-b′]dithiophene (820 mg, 4.3 mmol) in THF (100 mL) under argon at −78° C. was added a solution of n-butyllithium (2.5 M, 3.44 mL, 8.6 mmol). The solution was stirred at −78° C. for 30 minutes and then warmed to −20° C. for 30 minutes. Tri-n-butyltin chloride (2.34 mL, 8.6 mmol) was added and the reaction mixture was stirred at −20° C. for 30 minutes and then allowed to warm to room temperature. After 16 hours, hexane was added and the reaction was successively washed with water and brine, dried (MgSO4), concentrated and purified by flash chromatography (100% hexanes). 2,6-bis(tri-n-butylstannyl)-benzo[1,2-b:4,5-b′]dithiophene (1.4 g, 42%) was isolated along with product contaminated with the monostannylated benzodithiophene. 1H-NMR: 400 MHz, (CDCl3) δ: 8.27 (s, 2H), 7.38 (s, 2H), 1.65-1.57 (m, 12H), 1.41-1.32 (m, 12H), 1.26-1.11 (m, 12H), 0.91 (t, J=7.3 Hz, 18H) ppm.

Fuente