반응 #159212

반응 방정식

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

수율 42.0%

용매

THF

반응 조건

후처리

1. 1
   온도warmed to −20° C. for 30 minutes
2. 2
   workup.STIRRINGthe reaction mixture was stirred at −20° C. for 30 minutes
3. 3
   온도to warm to room temperature
4. 4
   workup.WAITAfter 16 hours
5. 5
   세척the reaction was successively washed with water and brine
6. 6
   건조dried (MgSO4)
7. 7
   농축concentrated
8. 8
   기타purified by flash chromatography (100% hexanes)

실험 절차

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.

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