1-Bromonaphthalene → HCID 57892505, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.161 g (0.715 millimole) of palladium (II) acetate in 20 ml of xylene was added 0.58 g (2.86 millimoles) of tri-tert-butylphosphine and the mixture was heated at 80° C. for 30 minutes with stirring. This solution was transferred into a solution heated at 80° C. of 5.24 g (0.0143 mole) of 2,7-bis(phenylamino)dibenzodioxin, 7.41 g (0.0358 mole) of 1-bromonaphthalene, and 5.77 g (0.06 mole) of sodium tert-butoxide in 260 ml of xylene. The mixture was heated up to 135° C. and heated at this temperature with stirring for 4 hours. The reaction mixture was cooled to room temperature, and 200 ml of water was added. The organic layer was separated from the aqueous layer, the aqueous layer was washed with 200 ml of toluene, and the organic layers were combined, concentrated, and dried under reduced pressure to give 9.5 g of a crude product. The crude product was subjected to reslurrying under heat with ethyl acetate and dried under reduced pressure to give 3.40 g (0.0055 mole, 38.5% yield) of 2,7-bis(N-1-naphthyl-N-phenylamino)dibenzodioxin. The product showed a purity of 98.3 area % (HPLC, 254 nm). The product was purified further by sublimation; FD-MS, m/z 618 [M]+, m.p. 315° C., Tg 103° C.

Provenance & Evidence