1-Bromooctane → 4,4,9,9-Tetraoctyl-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene

Participants

Reaction Conditions

Reaction Steps

To a 3-necked flask is added 4,9-dihydro-s-indaceno[1,2-b:5,6-b′]dithiophene (3.0 g, 11.3 mmol) and anhydrous DMSO (60 cm3) and the mixture is degassed for 20 minutes. To this mixture is added sodium tert-butoxide (6.69 g, 68.9 mmol) portion wise and the mixture is heated to 80° C. 1-Bromooctane (12 cm3, 69.5 mmol) is added dropwise over 30 minutes ensuring the reaction mixture temperature did not rise above 90° C. The mixture is then heated at 85° C. for 3 hours. The mixture allowed to cool to 70° C. and poured into ice-water (100 cm3). The product is extracted with DCM (2×200 cm3) and the combined organics washed with water (3×200 cm3), dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo. The crude product is purified by column chromatography (eluent: petroleum ether 40-60) to yield the product as a yellow oil, which crystallised to a yellow solid (2.83 g, 28%). 1H NMR (300 MHz, CDCl3): δ(ppm) 7.27 (s, 2H, Ar—H), 7.25 (d, J=4.9 Hz, 2H, Ar—H), 6.96 (d, J=4.9 Hz, 2H, Ar—H), 1.79-2.02 (m, 8H, CH2), 1.02-1.34 (m, 40H, CH2), 0.71-0.93 (m, 20H, CH3 & CH2). 13C NMR (75 MHz; CDCl3): δ(ppm) 155.1, 153.2, 141.6, 135.6, 126.1, 121.7, 113.1, 53.7, 39.2, 31.8, 30.0, 29.33, 29.25, 24.2, 22.6, 14.1.

Provenance & Evidence