反応 #492228

反応方程式

SnCl2

magnesium

4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophene-4,8-dione

10-bromodecylbenzene

magnesium

→

oil

収率 15.0%

4,8-bis(10-phenyldecyl)benzo[1,2-b:4,5-b′]dithiophene

収率 15.0%

溶媒

THF

brine

THF

反応条件

後処理

1. 1
   温度The mixture was heated
2. 2
   温度under reflux
3. 3
   その他was consumed
4. 4
   workup.ADDITIONwas added dropwise
5. 5
   温度After refluxing for 3 hours more
6. 6
   温度After cooling down
7. 7
   その他The organic phase was separated
8. 8
   乾燥dried over Na2SO4
9. 9
   その他The residue after vacuum evaporation
10. 10
    その他was purified by column chromatography with hexane/AcOEt 50:1 as eluent

実験手順

To a 100 mL flask under nitrogen was added magnesium (486 mg, 20 mmol) and anhydrous THF (10 mL). The mixture was heated under reflux and 10-bromodecylbenzene (5.95 g, 20 mmol) was added dropwise. The reaction mixture was kept under reflex temperatures until all magnesium was consumed. Subsequently, 4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophene-4,8-dione (1.1 g, 5.0 mmol) suspended in anhydrous THF (10 ml) was added dropwise. After refluxing for 3 hours more, it was cooled down to room temperature. SnCl2 solution (7.5 g in 19 mL 10% HCl) was slowly added dropwise and then the mixture was kept at 60° C. overnight. After cooling down, brine (25 mL) was added. The organic phase was separated and dried over Na2SO4. The residue after vacuum evaporation was purified by column chromatography with hexane/AcOEt 50:1 as eluent and gave a pale yellow oil (466 mg, yield 15%), which turned into a solid upon standing for a few days. 1H NMR (CDCl3, 500 MHz) δ=7.48 (d, J=6.0 Hz, 2H), 7.46 (d, J=5.0 Hz, 2H), 7.27-7.32 (m, 4H), 7.19 (d, J=7.0 Hz, 6H), 3.19 (t, J=8.0 Hz, 4H), 2.61 (t, J=7.5 Hz, 4H), 1.75-1.86 (m, 4H), 1.58-1.67 (m, 4H), 1.42-1.51 (m, 4H), 1.15-1.41 (m, 20H).

出典