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

HRID 1049669Notes

Reaction equation

HRID 1049669 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-triazineYield 36%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

50 g (92.5 mmol) of 2,4-bisbiphenyl-3-yl-6-(3-bromophenyl)-1,3,5-triazine and 13.8 g (93.2 mmol) of styreneboronic acid [2156-04-9] are dissolved in 300 ml of toluene, and 100 ml of a 2 M sodium carbonate solution are added. The reaction mixture is carefully degassed, 200 mg of tetrakistriphenylphosphinepalladium are added, and the mixture is heated under reflux for 20 h. The solution is cooled to room temperature, and 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. The residue is recrystallised from isopropanol, giving 18.8 g (33.3 mmol) (36%) of a white solid in a purity of 99.7%.

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 h
  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
  10. customThe residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-a432ff13d2834f77984db70d1c6b0858
Source dataset
uspto-grants-2016_07
Patent number
US09382253B2

Reaction notes

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