4-Bromobiphenyl → HCID 67337164, compound

HRID 1671829Notes

Reaction equation

HRID 1671829 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].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.BrC1C=CC([C:32]2[N:37]=[C:36]([C:38]3[C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[CH:41]=[CH:40][CH:39]=3)[N:35]=[C:34]([C:48]3[C:57]4[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=4)[CH:51]=[CH:50][CH:49]=3)[N:33]=2)=CC=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:38]1([C:36]2[N:35]=[C:34]([C:48]3[C:57]4[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=4)[CH:51]=[CH:50][CH:49]=3)[N:33]=[C:32]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][C:22]([C:3]5[CH:2]=[CH:1][CH:6]=[CH:5][CH:4]=5)=[CH:21][CH:20]=4)=[CH:15][CH:14]=3)[N:37]=2)[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 71014-BromobiphenylHCID 8058HexaneHCID 67336204HCID 67336204, compoundHCID 178418339Butyllithium

Product 1

HCID 67337164HCID 67337164, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Under a stream of argon, 2.8 ml of a hexane solution containing 4.3 mmol of butyl lithium was slowly added to 15 ml of tetrahydrofuran cooled to −78° C. in which prepared by dissolving 0.91 g of 4-bromobiphenyl. After stirring at −78° C. for 15 minutes, 1.19 g of dichloro(tetramethylethylenediamine)zinc(II) was added thereto and stirred at −78° C. for 10 minutes and then at room temperature for 2 hours. A 1.47 g portion of 2-(4-bromophenyl)-4,6-bis(1-naphthyl)-1,3,5-triazine prepared in Reference Example 4 and 0.14 g of tetrakis(triphenylphosphine)palladium(0) were dissolved in 80 ml of tetrahydrofuran and added to this solution, followed by stirring under heating reflux for 13 hours. The reaction solution was concentrated under a reduced pressure and the thus obtained solid was washed with chloroform to obtain a white solid of the intended 2,4-bis(1-naphthyl)-6-[1,1′:4′,1″]terphenyl-4-yl-1,3,5-triazine (1.19 g, yield 71%).

Workup

  1. customprepared
  2. stirringstirred at −78° C. for 10 minutes
  3. waitat room temperature for 2 hours
  4. additionadded to this solution
  5. stirringby stirring
  6. temperatureunder heating
  7. temperaturereflux for 13 hours
  8. concentrationThe reaction solution was concentrated under a reduced pressure
  9. washthe thus obtained solid was washed with chloroform

Sources & evidence

ORD record
ord-e7b83c1657e7429d848f5e5a8a24827d
Source dataset
uspto-grants-2011_08
Patent number
US07994316B2

Reaction notes

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