1-Bromonaphthalene → HCID 57892505, compound

HRID 905539Notes

Reaction equation

HRID 905539 reaction equation
[C:1](P(C(C)(C)C)C(C)(C)C)(C)(C)[CH3:2].[C:14]1([NH:20][C:21]2[CH:41]=[CH:40][C:24]3[O:25][C:26]4[CH:32]=[C:31]([NH:33][C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[CH:30]=[CH:29][C:27]=4[O:28][C:23]=3[CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Br[C:43]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45][CH:44]=1.CC(C)([O-])C.[Na+].[C:59]1([CH3:66])[C:60]([CH3:65])=[CH:61][CH:62]=[CH:63][CH:64]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[C:43]1([N:20]([C:21]2[CH:41]=[CH:40][C:24]3[O:25][C:26]4[CH:32]=[C:31]([N:33]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)[C:65]5[C:60]6[C:59](=[CH:64][CH:63]=[CH:62][CH:61]=6)[CH:66]=[CH:2][CH:1]=5)[CH:30]=[CH:29][C:27]=4[O:28][C:23]=3[CH:22]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45][CH:44]=1

Participants

9

Reactant 5

HCID 70011-BromonaphthaleneHCID 7237O-Xylene2×HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 57892504HCID 57892504, compound

Product 1

HCID 57892505HCID 57892505, compoundYield 38.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  1. temperatureThe mixture was heated up to 135° C.
  2. temperatureheated at this temperature
  3. stirringwith stirring for 4 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customThe organic layer was separated from the aqueous layer
  6. washthe aqueous layer was washed with 200 ml of toluene
  7. concentrationconcentrated
  8. customdried under reduced pressure
  9. customto give 9.5 g of a crude product
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-eb18b4e62a04466488466fc2a5dbf418
Source dataset
uspto-grants-2011_09
Patent number
US08012606B2

Reaction notes

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