3 7 dimethyloct 1 yne 3 73 g 27 mmol at rt the reaction mixture was heated up to 60 u00b0 c and kept stirring for 100 min it was cooled down to rt and benzo 1 2 b 4 5 b u2032 dithiophene 4 8 dione 1 g 4 53 mmol was added the reaction mixture was hated up to 60 u00b0 c and kept for 60 min it was then cooled to rt and 7 g sncl 2 in hcl solution 16 ml 10 was added dropwise to the reaction mixture the reaction mixture was heated at 65 u00b0 c for 60 min then cooled down to room temperature and poured into 100 ml water it was extracted with 50 ml hexanes twice the organic phase was combined and dried with anhydrous na 2 so 4 and the organic solvent was removed by vacuum evaporation the residue was purified by column chromatography on silica with hexanes dichloromethane 3 1 volume ratio yielding compound 10 1 88 g 90 to the solution of compound 2 1 88 g 4 07 mmol in 75 ml thf was added pd c 0 45 g 10 and reaction mixture was kept in a hydrogen atmosphere for 18 h at rt the mixture was filtered with celite and solvent was removed by vacuum.