反応 #492225

反応方程式

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

magnesium

2-ethylhexyl bromide

SnCl2

magnesium

→

oil

収率 43.0%

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

収率 43.0%

溶媒

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
   温度After cooling down
5. 5
   温度After refluxing for 1 hour 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 as eluent

実験手順

To a 100 mL flask under nitrogen was added magnesium (656 mg, 27 mmol) and anhydrous THF (10 mL). The mixture was heated under reflux and 2-ethylhexyl bromide (5.6 mL, mmol) was added dropwise. The reaction mixture was kept at refluxing temperatures until all magnesium was consumed. After cooling down, 4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophene-4,8-dione (1.1 g, 5.0 mmol) was added in one portion. After refluxing for 1 hour more, it was cooled down again 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. for 1 hour. After cooling down, brine (11 mL) was added. The organic phase was separated and dried over Na2SO4. The residue after vacuum evaporation was purified by column chromatography with hexane as eluent and gave a pale yellow oil (910 mg, yield 43%). 1H NMR (CDCl3, 500 MHz) δ=7.47 (d, J=6.0 Hz, 2H), 7.45 (d, J=6.0 Hz, 2H), 3.08-3.20 (m, 4H), 1.92-2.04 (m, 2H), 1.13-1.49 (m, 16H), 0.91 (t, J=7.0 Hz, 6H), 0.85 (t, J=7.0 Hz, 6H).

出典