4-Bromodiphenyl Ether → HCID 59317894, compound

HRID 2067704Notes

Reaction equation

HRID 2067704 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[CH:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)=[CH:13][CH:12]=1.C(P(C(C)(C)C)C1C=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(C)(C)C.P([O-])([O-])([O-])=[O:47].[K+].[K+].[K+].[C:54]([O:57][CH2:58][CH2:59][CH2:60]C)(=O)[CH3:55]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:17]([C:18]1[CH:23]=[CH:22][C:21]([N:8]2[C:3]3[C:2](=[CH:7][C:6]([CH2:60][CH2:59][C:58]([O:57][CH2:54][CH3:55])=[O:47])=[CH:5][CH:4]=3)[C:33]([CH2:32][CH2:31][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[CH:34]2)=[CH:20][CH:19]=1)[C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 5

HCID 75654-Bromodiphenyl Ether2×HCID 113411-Bromo-2-nitrobenzeneHCID 31272Butyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 27342152-(Di-tert-butylphosphino)biphenyl

Product 1

HCID 59317894HCID 59317894, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
120 °C

Procedure

The same reaction was performed as in Example 148 except for using, instead of the 2-bromonitrobenzene, 4-bromodiphenyl ether. That is, to a solution of the compound obtained at Example 142 (60 mg) in n-butyl acetate (4.5 ml) were added 4-bromodiphenyl ether (93 mg), palladium acetate (4.3 mg), 2-(di-tert-butylphosphino)biphenyl (11.4 mg) and tripotassium phosphate (161 mg), and the mixture was heated and stirred at 120° C. for 24 hours. The reaction mixture was cooled to room temperature, then the insolubles were filtered off, the filtrate was distilled off in vacuo and the residue obtained was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 3:2) to afford the above-identified compound (77 mg).

Workup

  1. customThe same reaction
  2. temperaturethe mixture was heated
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationthe insolubles were filtered off
  5. distillationthe filtrate was distilled off in vacuo
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 3:2)

Sources & evidence

ORD record
ord-5a77d989a9cf453ba212aafcd02e77e8
Source dataset
uspto-grants-2012_10
Patent number
US08293781B2

Reaction notes

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