반응 #731297

반응 방정식

1-chloro-6-iodohexane

2,2′-bithiophene

n-butyllithium

→

5-(6-chlorohexyl)-2,2′-bithiophene

수율 54.3%

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONAfter complete addition
2. 2
   기타The reaction was quenched with sat. aq. NH4Cl
3. 3
   추출the reaction mixture was extracted with ethyl acetate (3×100 ml)
4. 4
   세척The combined organic extracts were washed with water, brine
5. 5
   건조dried over sodium sulphate
6. 6
   기타The solvent was removed under reduced pressure
7. 7
   기타the residue was purified by column chromatography on silica
8. 8
   세척eluting with petroleum ether

실험 절차

To a stirred solution of 2,2′-bithiophene (10.0 g, 60.24 mmol) in anhydrous THF (150 ml) was added n-butyllithium (2.5 M in hexanes, 20.0 ml, 50.0 mmol) dropwise at −78° C. under nitrogen. After complete addition, the mixture was allowed to warm to room temperature, with stirring, over 2 h, followed by the addition of 1-chloro-6-iodohexane (14.55 g, 50.0 mmol). The resultant mixture was stirred overnight at room temperature. The reaction was quenched with sat. aq. NH4Cl, and the reaction mixture was extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with water, brine, and dried over sodium sulphate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica, eluting with petroleum ether, to give 5-(6-chlorohexyl)-2,2′-bithiophene as a white solid (7.73 g, 54%). 1H NMR (300 MHz, CDCl3): δ (ppm) 7.14 (d, J=5.3 Hz, 1.3 Hz, 1H, Ar—H), 7.08 (dd, J=3.5 Hz, 1.1 Hz, 1H, Ar—H), 6.97 (m, 2H, Ar—H), 6.66 (d, J=3.5 Hz, 1H, Ar—H), 3.51 (d, J=6.6 Hz, 2H, ClCH2), 2.78 (t, J=7.1 Hz 2H, ArCH2), 1.61-1.81 (m, 4H, CH2), 1.35-1.51 (m, 4H, CH2); MS (m/e): 282 (M+, 2%), 166 (8), 123 (39), 110 (22), 97 (100).

출처