Hexane → 5-Trimethylstannyl-4,4'-didodecyl-2,2'-bithiophene

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Reaction Conditions

Reaction Steps

To a solution of 5-bromo-4,4′-didodecyl-2,2′-bithiophene (29A, 100 mg, 0.172 mmol) in 4.0 mL of THF was added dropwise a solution of n-butyllithium in hexane (0.076 mL, 2.5 M, 0.189 mmol) at −78° C. The solution was stirred at −78° C. for 1 hour and a solution of trimethyltin chloride in THF (0.20 mL, 1.0 M, 0.20 mmol) was added in one portion. The solution was warmed to room temperature and 10.0 mL of water and 10.0 mL of diethylether were added. The organic layer was separated and washed twice with 20 mL of water and dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo to yield 5-trimethylstannyl-4,4′-didodecyl-2,2′-bithiophene (29, 0.103 g, 90% yield) as a yellow oil. 1H NMR (CDCl3): δ 0.84-1.64 (m, 46H), 2.58 (m, 4H), 6.77 (s, 1H), 6.99 (s, 1H), 7.13 (s, 1H).

Provenance & Evidence