反応 #159212

反応方程式

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

収率 42.0%

溶媒

THF

反応条件

後処理

1. 1
   温度warmed to −20° C. for 30 minutes
2. 2
   workup.STIRRINGthe reaction mixture was stirred at −20° C. for 30 minutes
3. 3
   温度to warm to room temperature
4. 4
   workup.WAITAfter 16 hours
5. 5
   洗浄the reaction was successively washed with water and brine
6. 6
   乾燥dried (MgSO4)
7. 7
   濃縮concentrated
8. 8
   その他purified by flash chromatography (100% hexanes)

実験手順

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.

出典