Stannous Chloride → HCID 86636741, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tin(II)chloride dehydrate (3.11 g, 9.2 mmol) in 50% acetic acid (50 ml) is added within ten minutes to a solution of 6,12-bis-trimethylsilanylethynyl-6,12-dihydro-dibenzo[d,d′]benzo[1,2-b;4,5-b′]dithiophene-6,12-diol (educt 5) (3.1 g, 6 mmol) in acetone (45 ml). There is a slight temperature increase (2-3° C.), and formation of a yellow suspension. This suspension is stirred over night at ambient temperature, and then the solid is filtered off. The solid is then washed with 50% acetic acid (twice with 30 ml), water (twice with 40 ml), and acetone (2*50 ml). The residue is then dried to give crude product which is filtered over a pad of silica (60 g) with chloroform to give product which is recrystallised from chloroform (35 ml). The product is filtered off, washed with chloroform (10 ml), and hexane (20 ml). After drying, the title product is obtained as yellow crystals. Mp. (DSC) 278° C. and 285° C. 1H-NMR (CDCl3, 300 MHz) δ 0.49 (s, 9H, SiCH3); 7.48-7.56 (m, 2H, H-2, H-3), 7.91 (d, 1H, H-4); 9.20 (d, 1H, H-1). 13C-NMR (CDCl3, 75 MHz) δ 0.28 (CH3); 101.79, 109.51 (C≡C); 112.56 (C-6); 122.93 (C-4); 124.66 (C-2); 125.14 (C-1); 127.72 (C-3); 132.91 (C-6a); 136.63 (C-6b); 140.73 (C-4-a); 143.11 (C-5a).

Provenance & Evidence