Sodium Carbonate → 2,4-Bisbiphenyl-3-yl-6-(4'-vinylbiphenyl-3-yl)-1,3,5-triazine

HRID 590898Notes

Reaction equation

HRID 590898 reaction equation
[C:1]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[C:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:16]=[CH:17][CH:18]=3)[N:10]=[C:9]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27](Br)[CH:26]=3)[N:8]=2)[CH:2]=1.[CH:38](B(O)O)=[CH:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[C:1]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[C:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:16]=[CH:17][CH:18]=3)[N:10]=[C:9]([C:25]3[CH:26]=[C:27]([C:43]4[CH:44]=[CH:45][C:40]([CH:39]=[CH2:38])=[CH:41][CH:42]=4)[CH:28]=[CH:29][CH:30]=3)[N:8]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343812-Phenylvinylboronic acidHCID 66666456HCID 66666456, compound

Product 1

HCID 666665312,4-Bisbiphenyl-3-yl-6-(4'-vinylbiphenyl-3-yl)-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

50 g of 2,4-bisbiphenyl-3-yl-6-(3-bromophenyl)-1,3,5-triazine and 13.8 g of styreneboronic acid [2156-04-9] are dissolved in 300 ml of toluene, and 100 ml of a 2M sodium carbonate solution are added. The reaction mixture is carefully degassed, and 200 mg of tetrakistriphenylphosphinepalladium are added, and the mixture is heated under reflux for 20 hours. The solution is cooled to room temperature. The phases are separated. The aqueous phase is extracted three times with toluene, the combined organic phases are subsequently washed twice with water, dried over magnesium sulfate, filtered, and the solvent is stripped off in vacuo.

Workup

  1. customThe reaction mixture is carefully degassed
  2. addition200 mg of tetrakistriphenylphosphinepalladium are added
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for 20 hours
  5. customThe phases are separated
  6. extractionThe aqueous phase is extracted three times with toluene
  7. washthe combined organic phases are subsequently washed twice with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered

Sources & evidence

ORD record
ord-5fb7c5cefc034e5f9564efd449a70a12
Source dataset
uspto-grants-2016_01
Patent number
US09236571B2

Reaction notes

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