4-Bromobiphenyl → 2,4-Bis(4-phenylphenyl)-6-[4-(4-phenylphenyl)phenyl]-1,3,5-triazine

HRID 1671828Notes

Reaction equation

HRID 1671828 reaction equation
CCCCCC.C([Li])CCC.Br[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.[C:25]1([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:30]=[CH:29][C:28]([C:31]2[N:36]=[C:35]([C:37]3[CH:42]=[CH:41][C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[CH:39][CH:38]=3)[N:34]=[C:33]([C:49]3[CH:54]=[CH:53][C:52](Br)=[CH:51][CH:50]=3)[N:32]=2)=[CH:27][CH:26]=1>O1CCCC1.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:25]1([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:30]=[CH:29][C:28]([C:31]2[N:36]=[C:35]([C:37]3[CH:42]=[CH:41][C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[CH:39][CH:38]=3)[N:34]=[C:33]([C:49]3[CH:54]=[CH:53][C:52]([C:22]4[CH:23]=[CH:24][C:19]([C:16]5[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=5)=[CH:20][CH:21]=4)=[CH:51][CH:50]=3)[N:32]=2)=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 71014-BromobiphenylHCID 8058HexaneHCID 673352762,4-Bisbiphenyl-4-yl-6-(4-bromophenyl)-1,3,5-triazineHCID 178418339Butyllithium

Product 1

HCID 673350422,4-Bis(4-phenylphenyl)-6-[4-(4-phenylphenyl)phenyl]-1,3,5-triazineYield 71%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Under a stream of argon, 2.1 ml of a hexane solution containing 3.3 mmol of butyl lithium was slowly added to 30 ml of tetrahydrofuran cooled to −78° C. in which prepared by dissolving 0.69 g of 4-bromobiphenyl. After stirring at −78° C. for 15 minutes, 0.91 g of dichloro(tetramethylethylenediamine)zinc(II) was added thereto and stirred at −78° C. for 10 minutes and then at room temperature for 2.5 hours. A 1.35 g portion of 2,4-bis(4-biphenylyl)-6-(4-bromophenyl)-1,3,5-triazine prepared in Reference Example 3 and 0.12 g of tetrakis(triphenylphosphine)palladium(0) were dissolved in 60 ml of tetrahydrofuran and added to this solution, followed by stirring under heating reflux for 2 hours. The reaction solution was concentrated under a reduced pressure, and the thus obtained solid was purified by a silica gel column chromatography (developing solvent hexane:chloroform=2:1 to chloroform) and then recrystallized from dichloromethane-methanol to obtain a white solid of the intended 2,4-bis(4-biphenylyl)-6-[1,1′:4′,1″]terphenyl-4-yl-1,3,5-triazine (1.09 g, yield 71%).

Workup

  1. customprepared
  2. stirringstirred at −78° C. for 10 minutes
  3. waitat room temperature for 2.5 hours
  4. additionadded to this solution
  5. stirringby stirring
  6. temperatureunder heating
  7. temperaturereflux for 2 hours
  8. concentrationThe reaction solution was concentrated under a reduced pressure
  9. customthe thus obtained solid was purified by a silica gel column chromatography (developing solvent hexane:chloroform=2:1 to chloroform)
  10. customrecrystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-871a41aa722247629699a9db2196c0c1
Source dataset
uspto-grants-2011_08
Patent number
US07994316B2

Reaction notes

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