Toluene → 2-(4-Bromophenyl)-6-phenylnaphthalene

HRID 1662915Notes

Reaction equation

HRID 1662915 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH:13]=[C:12](B(O)O)[CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(COC)OC>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([C:12]2[CH:11]=[CH:10][C:9]3[C:14](=[CH:15][CH:16]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:8]=3)[CH:13]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 57539613(6-Phenylnaphthalen-2-yl)boronic acid

Product 1

HCID 575398112-(4-Bromophenyl)-6-phenylnaphthaleneYield 48%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Under an argon gas atmosphere, 21.9 g (88.3 mmol) of 6-phenylnaphthalene-2-boronic acid, 25.0 g (88.3 mmol) of 4-bromoiodobenzene, 2.00 g (1.77 mmol) of tetrakis(triphenylphosphine) palladium(0), 400 mL of toluene, 100 mL of dimethoxyethane and 132 mL of 2M sodium carbonate solution were mixed, and stirred for 15 hours while being refluxed. After the reaction in the mixture was over, the mixture experienced filtration, through which aqueous phase thereof was eliminated. After organic phase thereof was cleansed by water and dried with magnesium sulfate, toluene was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 15.3 g of 2-(4-bromophenyl)-6-phenylnaphthalene was obtained with an yield of 48%.

Workup

  1. temperaturewhile being refluxed
  2. customAfter the reaction in the mixture
  3. filtrationfiltration
  4. dry with materialdried with magnesium sulfate, toluene
  5. distillationwas distilled away under reduced pressure
  6. customwas obtained with an yield of 48%

Sources & evidence

ORD record
ord-c577d53615314959a110599d4dea6944
Source dataset
uspto-grants-2011_10
Patent number
US08034256B2

Reaction notes

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