Tributyltin Chloride → Stannane, [2,2'-bithiophen]-5-yltributyl-

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Reaction Steps

The synthesis described herein is depicted schematically in FIG. 4. 1.0 g (6 mmol) of bithiophene in 30 ml THF was treated dropwise with 3.54 ml (6 mmol) of 1.70 M n-butyllithium and stiffed for 0.5 h at −78° C. under N2 atmosphere. 1.96 ml of tributylstannyl chloride (7.2 mmol) was then added to the solution. After stirring at room temperature for 6 h, the solvent was evaporated and the residue was dissolved in 20 ml of hexane and filtered. The filtrate was evaporated to produce 3.4 g of crude 5-(tributylstannyl)-2,2-bithiophene as a light yellow liquid for the next step reaction. 1H NMR: (250 MHZ, CDCl3): d (ppm) 7.27 (d, 1H), 7.15 (2d, 2H), 7.03 (d, 1H), 6.98 (t, 1H), 1.54 (m, 6H), 1.31 (m, 6H), 1.10 (t, 6H), 0.89 (m, 9H). 13C NMR (125 MHZ, CDCl3): d (ppm) 136.28, 127.98, 127.94, 125.19, 124.56, 124.17, 123.97, 123.66, 29.10, 27.50, 13.91, 11.11. MS (FAB): (M+) found: 456, calcd for C20H32S2Sn: 455.28.

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