again to u2212 78 u00b0 c and 2 77 ml 13 6 mmol 5 equiv of 2 isopropoxy 4 4 5 5 tetramethyl 1 3 2 dioxaborolane was added in one portion via syringe the reaction was stirred at u2212 78 u00b0 c for 1 hour and then allowed to warm to room temperature overnight the solution was poured into water and extracted with 4 u00d7 150 ml of methyl tert butyl ether the organic layers were combined and washed with 2 u00d7 150 ml of brine dried with anhydrous mgso 4 and filtered the solvent was removed under vacuum to yield and orange oil which was purified by column chromatography 5 etoac in hexanes to yield a colorless viscous oil 1 34 g 75 yield a 50 ml schlenk flask was charged with 0 309 g 0 472 mmol of 4h 4 4 bis 2 u2032 ethylhexyl cyclopenta 2 1 b 3 4 b u2032 dithiophene 2 6 bis pinacolborate ester prepared in example 9 0 367 g 0 510 mmol of 5 5 u2032 dibromo 3 u2033 4 u2033 dihexyl a pentathiophene its synthesis was described in wo 2005 092947 which is incorporated herein by reference 0 0013 g 0 00185 mmol of pdcl 2 pph 3 2 and 0 057 g 0 142 mmol of trioctylmethylammonium chloride aliquot 336 aldrich st louis mo the flask was fitted with a reflux condenser and the flask was evacuated and refilled with nitrogen three times the solids were dissolved in 6 ml of toluene and then 0 88 ml of 2m na 2 co 3 were added via syringe the reaction was then heated.