反应 #1884948

反应方程式

potassium iodide

4H-Cyclopenta[2,1-b:3,4-b′]dithiophene

hexyl bromide

→

4,4-Dihexyl-cyclopenta[2,1-b:3,4-b′]dithiophene

溶剂

dimethyl sulfoxide

反应条件

后处理

1. 1
   其他The mixture was purged with argon for 10 minutes
2. 2
   workup.ADDITIONfollowed by the slow addition of solid potassium hydroxide (2 g)
3. 3
   workup.ADDITIONThe mixture was then poured into de-ionized water (150 mL)
4. 4
   萃取the organic phase extracted with diethyl ether (4×100 mL)
5. 5
   其他The organic phases were collected
6. 6
   洗涤washed with brine (100 mL)
7. 7
   干燥The organic phase was dried over magnesium sulphate
8. 8
   过滤filtered
9. 9
   浓缩concentrated
10. 10
    其他to give the crude product as yellow oil
11. 11
    其他Purification via flash chromatography with hexanes (monitored at 254 nm, collected at 320 nm)
12. 12
    其他drying under high vacuum for 48 hours
13. 13
    其他gave pure product as colorless oil

实验过程

To a solution of 4H-Cyclopenta[2,1-b:3,4-b′]dithiophene (CDT) (1.63 g, 9.14 mmol) in dimethyl sulfoxide (50 mL) was added hexyl bromide (3.1 g, 18.9 mmol) and a catalytic amount of potassium iodide (50 mg). The mixture was purged with argon for 10 minutes followed by the slow addition of solid potassium hydroxide (2 g). The now dark green mixture was stirred in the dark at room temperature for 72 hours. The mixture was then poured into de-ionized water (150 mL) and the organic phase extracted with diethyl ether (4×100 mL). The organic phases were collected and washed with brine (100 mL) and a saturated ammonium chloride solution (100 mL). The organic phase was dried over magnesium sulphate, filtered, and concentrated to give the crude product as yellow oil. Purification via flash chromatography with hexanes (monitored at 254 nm, collected at 320 nm) and drying under high vacuum for 48 hours gave pure product as colorless oil. Yield 2.8 g (88%). 1H NMR (500 MHz, CDCl3): δ=7.15 (d, 2H, 3JH-H=5 Hz), 6.94 (d, 2H, 3JH-H=5 Hz), 1.84 (m, 4H, C—CH2), 1.19 (m, 12H, alkyl-CH2), 0.95 (m, 4H, alkyl-CH2), 0.82 (m, 6H, alkyl-CH3).

来源