반응 #992721

반응 방정식

2,7-bis(phenylamino)dibenzodioxin

1-bromonaphthalene

sodium tert-butoxide

xylene

tri-tert-butylphosphine

xylene

→

2,7-bis(N-1-naphthyl-N-phenylamino)dibenzodioxin

수율 38.5%

용매

ethyl acetate

water

반응 조건

후처리

1. 1
   온도The mixture was heated up to 135° C.
2. 2
   온도heated at this temperature
3. 3
   workup.STIRRINGwith stirring for 4 hours
4. 4
   온도The reaction mixture was cooled to room temperature
5. 5
   기타The organic layer was separated from the aqueous layer
6. 6
   세척the aqueous layer was washed with 200 ml of toluene
7. 7
   농축concentrated
8. 8
   기타dried under reduced pressure
9. 9
   기타to give 9.5 g of a crude product
10. 10
    기타dried under reduced pressure

실험 절차

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.

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