Tetrahydrofuran → 2,4-Bis-(4-tert-butylphenyl)-6-(4'-vinylbiphenyl-4-yl)-1,3,5-triazine

HRID 1628369Notes

Reaction equation

HRID 1628369 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=3)[N:11]=[C:10]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=3)[N:9]=2)=[CH:4][CH:3]=1.C(OB([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)O)=C.C(=O)([O-])[O-].[Na+].[Na+].[CH2:51]1COC[CH2:52]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:20]([C:17]1[CH:18]=[CH:19][C:14]([C:12]2[N:11]=[C:10]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:28][CH:29]=3)[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:42]4[CH:41]=[CH:40][C:39]([CH:51]=[CH2:52])=[CH:44][CH:43]=4)=[CH:3][CH:4]=3)[N:13]=2)=[CH:15][CH:16]=1)([CH3:22])([CH3:23])[CH3:21]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 594397872-(4-Bromophenyl)-4,6-bis(4-tert-butylphenyl)-1,3,5-triazineHCID 66674744Ethenoxy(phenyl)borinic acid

Product 1

HCID 594397822,4-Bis-(4-tert-butylphenyl)-6-(4'-vinylbiphenyl-4-yl)-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

2.0 g (0.0040 mol) of 2-(4-bromophenyl)-4,6-bis-(4-tert-butylphenyl)-1,3,5-triazine and 0.8878 g (0.006 mol) of vinylphenylboronic acid and 0.050 g (0.0432 mmol) of Pd(PPh3)4 are initially introduced. After addition of 26 ml of sodium carbonate solution and 54 ml of THF, the mixture is brought to reaction under reflux for 24 h. For work-up, the mixture is filtered through Celite and taken up in ethyl acetate. The organic phase is extracted a number of times with water. The solvent of the combined organic phases is removed completely. A recrystallisation is carried out from chloroform/ethanol, and subsequent column chromatography is carried out with hexane:ethyl acetate. After the column chromatography, 1.6 g (76%) of clean substance are isolated.

Workup

  1. customthe mixture is brought to reaction
  2. temperatureunder reflux for 24 h
  3. filtrationFor work-up, the mixture is filtered through Celite
  4. extractionThe organic phase is extracted a number of times with water
  5. customThe solvent of the combined organic phases is removed completely
  6. customA recrystallisation
  7. customAfter the column chromatography, 1.6 g (76%) of clean substance are isolated

Sources & evidence

ORD record
ord-639465824ba44125be47b249a50c6c3c
Source dataset
uspto-grants-2014_07
Patent number
US08786181B2

Reaction notes

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