Sodium Carbonate → 6-Bromo-2,2'-binaphthalene

HRID 1625302Notes

Reaction equation

HRID 1625302 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Br:12])[CH:8]=2)[CH:3]=1.[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1B(O)O.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.C(COC)OC>[Br:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:15]3[CH:14]=[CH:13][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=3)[CH:3]=2)[CH:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6405912,6-DibromonaphthaleneHCID 2734375(Naphthalen-2-yl)boronic acid

Product 1

HCID 575399876-Bromo-2,2'-binaphthaleneYield 69%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Under an argon gas atmosphere, 246 g (860 mmol) of 2,6-dibromonaphthalene, 163 g (950 mmol) of 2-naphthalene boronic acid, 20 g (17.0 mmol) of tetrakis(triphenylphosphine)palladium(0), 3 L of dimethoxyethane (DME) and 1.5 L of 2M sodium carbonate solution were mixed, and stirred for 16 hours while being refluxed. After the completion of the reaction, precipitated crystal was separated by filtration. Then, the obtained solid was cleansed with water, methanol and hexane. The obtained solid was dried under reduced pressure, and 197 g of 2-bromo-6-(2-naphthyl)naphthalene was obtained at an yield of 69%.

Workup

  1. temperaturewhile being refluxed
  2. customAfter the completion of the reaction
  3. customprecipitated crystal
  4. customwas separated by filtration
  5. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-b4688e203477453abc3b2fd7348c8ccf
Source dataset
uspto-grants-2014_07
Patent number
US08779655B2

Reaction notes

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