Reacción #731297

Ecuación de reacción

1-chloro-6-iodohexane

2,2′-bithiophene

n-butyllithium

→

5-(6-chlorohexyl)-2,2′-bithiophene

Rendimiento 54.3%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente