Toluene → HCID 131734703, compound

HRID 1773059Notes

Reaction equation

HRID 1773059 reaction equation
Cl[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[CH:8][CH:7]=[N:6]3)[N:3]=1.C1(C2C=CC=CC=2)C=CC=CC=1[N:22]1[CH:27]=[N:26][C:25]([C:28]2[CH:33]=[C:32](B3OC(C)(C)C(C)(C)O3)[CH:31]=[C:30](B3OC(C)(C)C(C)(C)O3)[CH:29]=2)=[N:24][CH2:23]1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+].[C:66]1([CH3:72])[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[C:66]1([C:72]2[CH:12]=[CH:13][CH:4]=[CH:5][CH:10]=2)[CH:71]=[CH:70][CH:69]=[CH:68][C:67]=1[N:22]1[CH:27]=[N:26][C:25]([C:28]2[CH:29]=[C:30]([C:2]3[CH:15]=[CH:14][C:13]4[C:4](=[C:5]5[C:10](=[CH:11][CH:12]=4)[CH:9]=[CH:8][CH:7]=[N:6]5)[N:3]=3)[CH:31]=[C:32]([C:7]3[CH:8]=[CH:9][C:10]4[C:5](=[C:4]5[C:13](=[CH:12][CH:11]=4)[CH:14]=[CH:15][CH:2]=[N:3]5)[N:6]=3)[CH:33]=2)=[N:24][CH2:23]1

Participants

8

Reactant 5

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 3551932-Chloro-1,10-phenanthrolineHCID 433294Lithium ChlorideHCID 131734704HCID 131734704, compound

Product 1

HCID 131734703HCID 131734703, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

In a stream of argon, 1.13 g of 2-chloro-1,10-phenanthroline, 1.57 g of 2,4-di(3-biphenylyl-6-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-1,3,5-triazine, 280 mg of lithium chloride and 203 mg of tetrakis(triphenylphosphine)palladium were suspended in a toluene (60 mL)/ethanol (15 mL) mixed solvent. 8.8 mL of a 2.0 M aqueous sodium carbonate solution was added in the obtained suspension, and the mixture was stirred at 100° C. for 65 hours. Then the reaction mixture was left to be cooled to room temperature, and distilled under a reduced pressure to remove low-boiling point ingredients. The thus-obtained residue was purified by alumina column chromatography using chloroform as a developing solvent to give 1.22 g of target 2,4-di(3-biphenylyl-6-[3,5-bis(1,10-phenanthrolin-2-yl)phenyl]-1,3,5-triazine as a white powder (yield, 68%).

Workup

  1. additionmixed solvent
  2. waitThen the reaction mixture was left
  3. temperatureto be cooled to room temperature
  4. distillationdistilled under a reduced pressure
  5. customto remove low-boiling point ingredients
  6. customThe thus-obtained residue was purified by alumina column chromatography
  7. customto give 1.22 g of target 2,4-di(

Sources & evidence

ORD record
ord-a647b43b884e43588fceaa35edfa4ea2
Source dataset
uspto-grants-2016_02
Patent number
US09252368B2

Reaction notes

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