ch 2 cl 2 0 5 g 0 6 mmol was then added to the solution and the reaction mixture was bubbled with nitrogen for 15 minutes the resultant mixture was refluxed for 12 hours after cooling h 2 o 1 ml was added and stirred for 15 min the reaction mixture was filtered through a silica pad and washed with 75 ch 2 cl 2 hexane the solvent was removed in vacuo and the residue was purified by flash chromatography using 25 40 ch 2 cl 2 hexane to afford n phenyl n 4 4 4 5 5 tetramethyl 1 3 2 dioxaborolan 2 yl phenyl dibenzo b d thiophen 4 amine 5 9 g 64 yield as a white solid to a solution of n phenyl n 4 4 4 5 5 tetramethyl 1 3 2 dioxaborolan 2 yl phenyl dibenzo b d thiophen 4 amine 5 9 g 12 4 mmol 3 bromocabazole 3 5 g 14 2 mmol k 2 co 3 16 6 g 120 0 mmol in toluene 150 ml water 50 ml and etoh 50 ml was bubbled for 30 min pd pph 3 4 0 4 g 0 4 mmol was added the mixture was bubbled for 15 min the resultant mixture was refluxed for 12 h after cooling the reaction mixture was extracted by ch 2.