1,2-Dimethoxyethane → HCID 15311215, compound

HRID 1045300Notes

Reaction equation

HRID 1045300 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([Br:21])[CH:17]=2)[CH:12]=1.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>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.O.C1(C)C=CC=CC=1>[Br:21][C:16]1[CH:15]=[CH:14][C:13]2[C:18](=[CH:19][CH:20]=[C:11]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:12]=2)[CH:17]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 6405912,6-Dibromonaphthalene

Product 1

HCID 15311215HCID 15311215, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 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 2,6-dibromonaphthalene, 24.2 g (21.0 mmol) of tetrakis(triphenylphosphine)palladium(0), 4.3 L of dimethoxyethane and 1.60 L of aqueous solution of 2M sodium carbonate were added together, and stirred at 78 degrees C. for 24 hours. The reaction mixture was added with toluene and water, and aqueous phase thereof was eliminated. After organic phase thereof was washed by water and dried with magnesium sulfate, the toluene was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography and recrystallized with hexane such that 108 g of 2-bromo-6-phenylnaphthalene was obtained at an yield of 36%.

Workup

  1. washAfter organic phase thereof was washed by water
  2. dry with materialdried with magnesium sulfate
  3. distillationthe toluene was distilled away under reduced pressure
  4. customrecrystallized with hexane such that 108 g of 2-bromo-6-phenylnaphthalene
  5. customwas obtained at an yield of 36%

Sources & evidence

ORD record
ord-b207ff3df8354da98caf2db4bd650ada
Source dataset
uspto-grants-2013_10
Patent number
US08568903B2

Reaction notes

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