1,2-Dimethoxyethane → 1-Bromo-4-phenylnaphthalene

HRID 912397Notes

Reaction equation

HRID 912397 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([Br:21])=[CH:13][CH:12]=1.C(COC)OC.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.O.C1(C)C=CC=CC=1>[Br:21][C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 665211,4-DibromonaphthaleneHCID 66827Phenylboronic Acid

Product 1

HCID 122750251-Bromo-4-phenylnaphthaleneYield 41.1%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
78 °C

Procedure

Under an argon gas atmosphere, 128.0 g (1.049 mol) of phenylboronic acid, 300.0 g (1.163 mol) of 1,4-dibromonaphthalene, 24.2 g (21.0 mmol) of tetrakis(triphenylphosphine) palladium(0), 4.3 L of dimethoxyethane and 1.60 L of 2M sodium carbonate solution were mixed, and stirred for 24 hours at 78 degrees C. The reaction mixture was further added with toluene and water, and then 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. By refining residue thereof by silica-gel column chromatography and by recrystallizing the residue by hexane, 122 g of 1-bromo-4-phenyl naphthalene was obtained with an yield of 41%.

Workup

  1. dry with materialdried with magnesium sulfate, toluene
  2. distillationwas distilled away under reduced pressure
  3. customby silica-gel column chromatography and by recrystallizing the residue by hexane

Sources & evidence

ORD record
ord-a4bce087412146a8a72d8d88035279ce
Source dataset
uspto-grants-2011_09
Patent number
US08025815B2

Reaction notes

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