Potassium Phosphate, Tribasic → HCID 131736878, compound

Participants

Reaction Conditions

Reaction Steps

2,8-dibromo-6,6,12,12-tetraoctyl-6,12-dihydroindeno[1,2-b]fluorene (2.60 g), 2-(4-(bis(4-bromophenyl)amino)phenyl)-2-methylpropanenitrile (947 mg), 2-(4-(bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)amino)phenyl)-2-methylpropanenitrile (2.84 g), potassium phosphate (4.27 g) and Aliquat 336 (2 drops) were dissolved in a mixture of toluene (32 mL), dioxane (16 mL) and water (16 mL). The solution was degassed for 15 minutes before adding tris(dibenzylideneacetone)dipalladium(0) (23 mg) and tri(o-tolyl)phosphine (46 mg) and heating to 90° C. for 17 hours. The reaction mixture was poured onto methanol (320 mL) and the resulting precipitate was filtered, dissolved in toluene (200 mL), washed with 1N NaOH, brine, water, dried (MgSO4) and concentrated. The residue was dissolved in toluene (150 mL) and passed through a pad of silica, washing through with toluene, toluene/THF and THF. The filtrates were concentrated and charcoal treated (3×0.53 g). The filtrates were concentrated and the solid taken up in THF (70 mL) and added dropwise to methanol (350 mL). The solid was filtered to give the target compound as a yellow solid. Yield: 3.3 g. Mn=11341 g/mol, n=11.2, Polydispersity=1.9.

Provenance & Evidence