Thiophene → 2-Dodecylthiophene

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A solution of thiophene (14.3 g, 0.17 mol) in dry THF (150 mL) was cooled to −78° C. under nitrogen. A solution of n-BuLi (38.0 mL, 2.5 M, 95.0 mmol) was then added dropwise over a course of 40 minutes. After addition, the reaction mixture was stirred at −78° C. for additional 2 hours, before a solution of n-C12H25Br (16.9 g, 67.8 mmol) in dry THF (25 mL) was added slowly. This mixture was stirred at −78° C. for 1 hour, and then allowed to warm to room temperature slowly and stirred at room temperature overnight. The reaction was quenched by water (20 mL) and the mixture was poured into water (400 mL), and the resulting mixture was extracted with ether (400 mL). The organic layer was washed with water and brine, dried over MgSO4, and concentrated on a rotary evaporator. The residue was subjected to column chromatography on silica gel with hexane as eluent, leading to a colorless oil as the product. (8.68 g, 50.7%)

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