Toluene → HCID 86669959, compound

HRID 2273502Notes

Reaction equation

HRID 2273502 reaction equation
[CH:1]1[C:14]2[CH:13]=[C:12](B(O)O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:18][C:19]1[CH:20]=[C:21]([C:26]2[N:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:29]=[C:28]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:27]=2)[CH:22]=[C:23](Br)[CH:24]=1.C1(C)C=CC=CC=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:38]1([C:28]2[N:29]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:31]=[C:26]([C:21]3[CH:22]=[C:23]([C:12]4[C:11]5[C:6]([C:5]6[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=6[CH:13]=4)=[CH:7][CH:8]=[CH:9][CH:10]=5)[CH:24]=[C:19]([Br:18])[CH:20]=3)[N:27]=2)[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 117757049-Phenanthracenylboronic acidHCID 583826152-(3,5-Dibromophenyl)-4,6-diphenyl-1,3,5-triazine

Product 1

HCID 86669959HCID 86669959, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

In a stream of argon, 0.71 g (3.21 mmol) of 9-phenanthreneboronic acid, 1.50 g (3.21 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 37.0 mg (0.0321 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 120 mL of toluene and 15 mL of ethanol, and the resultant suspension was heated to 60° C. and maintained at that temperature for 12 hours while being stirred. The obtained reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (2:1) mixed solvent as an eluent to give 0.54 g of the target 4,6-diphenyl-2-[5-(9-phenanthryl)-3-bromophenyl]-1,3,5-triazine as a white solid (yield: 30%).

Workup

  1. temperaturemaintained at that temperature for 12 hours
  2. customThe obtained reaction mixture
  3. distillationdistilled under a reduced pressure
  4. customto remove all volatile materials
  5. additionMethanol was added to the concentrate
  6. filtrationthe thus-deposited solid was collected by filtration
  7. customThe obtained crude product
  8. customwas purified by silica gel chromatography
  9. additionmixed solvent as an eluent

Sources & evidence

ORD record
ord-c04f602bc6de485ca5a24909a201fa90
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

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