Toluene → HCID 90401604, compound

HRID 1773061Notes

Reaction equation

HRID 1773061 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.[C:16]1(C2C=CC=CC=2)[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[N:27]=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30](B3OC(C)(C)C(C)(C)O3)[CH:29]=2)[N:25]=[CH:24][N:23]=1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+].[C:57]1(C)[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=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:31]1([C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[CH:32]=[CH:33][C:28]([C:26]2[N:27]=[C:22]([C:17]3[CH:18]=[CH:19][C:20]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:21][CH:16]=3)[N:23]=[C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:2]4[CH:15]=[CH:14][C:13]5[C:4](=[C:5]6[C:10](=[CH:11][CH:12]=5)[CH:9]=[CH:8][CH:7]=[N:6]6)[N:3]=4)[CH:29]=3)[N:25]=2)=[CH:29][CH:30]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 3551932-Chloro-1,10-phenanthrolineHCID 433294Lithium ChlorideHCID 131734705HCID 131734705, compound

Product 1

HCID 90401604HCID 90401604, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

In a stream of argon, 700 mg of 2-chloro-1,10-phenanthroline, 1.60 g of 2,4-di(4-biphenylyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine, 346 mg of lithium chloride and 126 mg of tetrakis(triphenylphosphine)palladium were suspended in a toluene (64 mL)/ethanol (16 mL) mixed solvent. 5.4 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 a hexane/chloroform (1:2 to 1:3) mixed solvent as a developing solvent, and then recrystallized from a dichloromethane/methanol mixed solvent to give 1.58 g of target 2,4-di(4-biphenylyl)-6-[3-(1,10-phenanthrolin-2-yl)phenyl]-1,3,5-triazine as a white powder (yield, 91%).

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. additionmixed solvent as a developing solvent
  8. customrecrystallized from a dichloromethane/methanol mixed solvent
  9. customto give

Sources & evidence

ORD record
ord-23ee31d374bf4238815da1a9b48720f9
Source dataset
uspto-grants-2016_02
Patent number
US09252368B2

Reaction notes

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