Stannous Chloride → 6,12-Bis[2-[4-(1,1-dimethylethyl)phenyl]ethynyl]benzo[1,2-b:4,5-b′]bis[1]benzothiophene

Participants

Reaction Conditions

Reaction Steps

A solution of tin(II)chloride dehydrate (1.82 g, 8.05 mmol) in glacial acetic acid (30 ml) is added within ten minutes to a solution of 6,12-bis-(4-tert-butyl-phenylethynyl)-6,12-dihydro-dibenzo[d,d′]benzo[1,2-b;4,5-b′]dithiophene-6,12-diol (educt 2) in acetone (30 ml). There is a slight temperature increase (8° C.), and formation of a yellow suspension takes place. This suspension is stirred over night at ambient temperature, and then the solid is filtered off. The solid is then washed with water/glacial acetic acid (twice, 30 ml 1:1 v:v), water (twice with 30 ml), and twice with acetone (30 ml). The residue is then dried to give crude product which is recrystallised from anisol (65 ml). The product is filtered off, washed with anisol (8 ml), toluene (2 times 8 ml) and hexane (twice ca. 10 ml) and dried to give the title product as yellow crystals. Mp. (DSC) 349-350° C., MS (m/z 602 (100%), correct isotopic pattern), elementary analysis: C, 84.61%; (calcd. 83.68%); H, 5.89%; (calcd. 5.68%). 1H-NMR (CDCl3, 300 MHz) δ 1.33 (s, 9H, C(CH3)3); 7.41-7.47 (m, 4H, 2 Ph H, 2 benzothiophene H); 7.66 (AA′BB′, 2H, 2 Ph H); 7.84 (m, 1H), 9.15 (m, 1H) (2 benzothiophene H).

Provenance & Evidence