Tris(o-methoxyphenyl)phosphine → 1,6-Di(quinolin-8-yl)pyrene

HRID 2285340Notes

Reaction equation

HRID 2285340 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2B(O)O)[CH:4]=[CH:3][CH:2]=1.CCCCCCCC([C:23]([NH3+:42])([C:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=O)C(CCCCCCC)=O)=O.[Cl-].COC1C=CC=CC=1P(C1C=CC=CC=1OC)C1C=CC=CC=1OC.O.C(=O)([O-])[O-].[Na+].[Na+].Br[C:77]1[CH:78]=[C:79]2[C:91]3=[C:92]4[C:82](=[CH:83][C:84](Br)=[CH:85][C:86]4=[CH:87][CH:88]=[C:89]3[CH:90]=1)[CH:81]=[CH:80]2>[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:85]2[C:86]3[C:92]4=[C:91]5[C:89](=[CH:88][CH:87]=3)[CH:90]=[CH:77][C:78]([C:33]3[CH:35]=[CH:36][CH:37]=[C:38]6[C:23]=3[N:42]=[CH:41][CH:40]=[CH:39]6)=[C:79]5[CH:80]=[CH:81][C:82]4=[CH:83][CH:84]=2)[CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 5

HCID 78464Tris(o-methoxyphenyl)phosphineHCID 27343808-Quinolineboronic acidHCID 2735133Sodium Carbonate MonohydrateHCID 136154792,7-DibromopyreneHCID 77620884Tricaprylylmethyl ammonium chloride2×

Product 1

HCID 867117241,6-Di(quinolin-8-yl)pyreneYield 48%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Quinoline-8-boronic acid (2.2 g, 12.2 mmol), trioctylmethylammonium chloride (trademark name: Aliquat336 (hereinafter referred to as Aliquat336), prepared by Aldrich Corporation, 0.74 g), palladium acetate (1.3 mg), tris(o-methoxyphenyl)phosphine (13.3 mg), toluene (58 ml), and sodium carbonate water solution (17.8 mmol) were added to dibromo pyrene (2.0 g, 5.6 mmol) synthesized in the prepared example and they were agitated at a temperature of 100° C. of four hours. A crystal was obtained by cooling the resultant reaction liquid at room temperature and filtering the cooled reaction (including the crystal). The compound B of 1.8 g was obtained by washing the crystal in an order of toluene, water, and methanol, and drying the washed crystal under reduced pressure (yield 48%).

Workup

  1. customA crystal was obtained
  2. temperatureby cooling the resultant
  3. customreaction liquid at room temperature
  4. filtrationfiltering
  5. customthe cooled reaction (

Sources & evidence

ORD record
ord-22f685f4ef5a431a95a086a1047537dc
Source dataset
uspto-grants-2015_09
Patent number
US09147846B2

Reaction notes

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