Stannous Chloride → HCID 57995463, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tin(II)chloride dehydrate (2.59 g, 11.5 mmol) in 50% acetic acid (40 ml) is added within ten minutes to a solution of 6,12-bis-[(triisopropylsilanyl)-ethynyl]-6,12-dihydro-dibenzo[d,d′]benzo[1,2-b;4,5-b′]dithiophene-6,12-diol (educt 3) in acetone (35 ml). There is a slight temperature increase (2-3° 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 50% acetic acid (30 ml), water (twice with 40 ml), and acetone (2*40 ml). The residue is then dried to give crude product which is recrystallised from toluene (15 ml). The product is filtered off, washed with toluene (10 ml), and hexane (10 ml). After drying, the title product is obtained as pale yellow crystals. Mp. (DSC) 155° C. (broad probably phase transition), 208° C. (sharp, probably melting point). 1H-NMR (CDCl3, 300 MHz) δ 1.31-1.336 (m (higher order), 21H, CH(CH3)2); 7.48 (m, 1H, H-2), 7.53 (m, 1H, H-3), 7.92 (d, 1H, H-4); 9.37 (d, 1H, H-1). 13C-NMR (CDCl3, 75 MHz) δ 11.92 (CH); 19.22 (CH3); 103.42, 106.36 (C≡C); 112.56 (C-6); 122.78 (C-4); 124.33 (C-2); 125.16 (C-1); 127.46 (C-3); 132.78 (C-6a); 135.49 (C-6b); 140.47 (C-4-a); 143.30 (C-5a).

Provenance & Evidence