Trimethyl borate → HCID 58251291, compound

Participants

Reaction Conditions

Reaction Steps

28.9 g (103 mmol) of bromopyrene are dissolved in 275 ml of dry THF, the solution is cooled to −75° C., and 52 ml (104 mmol) of a 2 M solution of n-butyllithium are added dropwise at this temperature. The yellow suspension is stirred at −75° C. for 1 h, and 17.5 ml (155 mmol) of trimethyl borate are then added dropwise. After the mixture has been warmed to RT, 34.5 g (103 mmol) of diethyl chlorobromoterephthalate, 22 g (206 mmol) of Na2CO3, 1.2 g (1.03 mmol) of tetrakis(triphenylphosphine)palladium(0), 140 ml of H2O, 280 ml of toluene and 140 ml of EtOH are added, and the mixture is heated at the boil for 2 h. After the organic phase has been separated off, washed twice with water and dried over Na2SO4, the solvent is removed in vacuo, and the oil which remains is brought to crystallisation in heptane. Recrystallisation twice gives the product in the form of a colourless solid (33 g, 70%) and a purity of >98%, which is employed in this form in the subsequent reaction.

Provenance & Evidence