反应详情

温度

0 °C

To a solution of 4,4′-didodecyl-2,2′-bithiophene (0.100 g, 0.199 mmol) in CHCl3/HOAc (1:1) (Vt=2.0 mL) at 0° C. was added N-bromosuccimide (NBS, 35.7 mg, 0.199 mmol) in portions over a period of 45 minutes. The reaction mixture was stirred for 1 hour at 0° C. and overnight at room temperature. The reaction mixture was poured into water (50.0 mL) and extracted with chloroform (3×50.0 mL). The combined organic phases were washed with water (50.0 mL), NaOH solution, and dried over MgSO4. After filtration through Celite, the filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel (hexanes) to provide 5-bromo-4,4′-didodecyl-2,2′-bithiophene (29A) as a colorless oil (98.0 mg, 85% yield). 1H NMR (CDCl3): δ 0.84-1.54 (m, 46H), 2.57 (m, 4H), 6.81 (s, 1H), 6.84 (s, 1H), 6.94 (s, 1H).

1. extractionextracted with chloroform (3×50.0 mL)
2. washThe combined organic phases were washed with water (50.0 mL), NaOH solution
3. dry with materialdried over MgSO4
4. filtrationAfter filtration through Celite
5. concentrationthe filtrate was concentrated in vacuo
6. customthe residue was purified by column chromatography on silica gel (hexanes)