Tetrahydrofuran → 3,6-Didodecylthieno[3,2-b]thiophene

Participants

Reaction Conditions

Reaction Steps

A 20 mL glass vial is charged with 3,6-dibromothieno[3,2-b]thiophene (1.00 g, 3.36 mmol) and Pd(dppf)Cl2 (0.14 g, 0.17 mmol, 5 mol %), and purged with nitrogen for 10 minutes. A 0.5M solution of dodecylzinc bromide in anhydrous THF (15 mL, 7.5 mmol) is added. The glass vial is placed into a microwave reactor (Emrys Creator, Personal Chemistry Ltd) and heated at 150° C. for 10 minutes with stirring. After cooling to RT, the reaction mixture is diluted with diethyl ether (100 mL) and quenched with 5% hydrochloric acid (50 mL). The organic layer is separated and the aqueous layer is re-extracted with diethyl ether (100 mL). The combined extracts are washed with water (2×50 mL), dried over sodium sulphate, and concentrated in vacuo. The crude product is filtered through a short plug of silica, eluting with petroleum ether 40-60. Recrystallisation from 2-butanone yielded the product as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 6.95 (s, 2H), 2.70 (t, 4H), 1.74 (m, 4H), 1.22-1.42 (br, 36H), 0.88 (t, 6H). 13C NMR (75 MHz, CDCl3) δ 139.3, 135.5, 120.8, 31.9, 29.8, 29.69, 29.67, 29.6, 29.42, 29.37, 28.7, 22.7, 14.2.

Provenance & Evidence