2-(Tri-n-butylstannyl)thiophene → HCID 66831870, compound

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Reaction Steps

4,7-Dibromo-2-dodecylbenzotriazole (100 mg, 0.224 mmol), and tributyl(thiophen-2-yl)stannane were dissolved in anhydrous THF (100 ml) and dichlorobis (triphenylphosphine)-palladium(II) (50 mg, 0.045 mmol) was added at room temperature. The mixture was refluxed for 12 hours under argon atmosphere. Solvent was evaporated under vacuum and the crude product was purified by column chromatography on silica gel to obtain 75 mg (74%) TBT. 1H NMR (400 MHz, CDCl3, δ): 8.01 (d, J=5.6 Hz, 2H), 7.52 (s, 2H), 7.28 (d, J=6.0 Hz, 2H), 7.09 (t, JA=8.8 Hz, JB=4.8, 2H), 4.60 (t, J=7.0 Hz, 2H), 2.10 (m, 2H), 1.38-1.15 (m, 18H), 0.80 (t, J=6.9 Hz, 3H); 13C NMR (100 MHz, DMSO-d6, δ): 142.4, 140.2, 128.4, 127.3, 125.8, 123.9, 123.0, 57.1, 32.2, 30.3, 29.9, 29.8, 29.7, 29.6, 29.5, 29.3, 26.9, 22.9, 14.4. MS (m/z): 451 [M+]

Provenance & Evidence