Sodium Carbonate → 1-Bromo-4-(2-formylphenyl)naphthalene

HRID 2274123Notes

Reaction equation

HRID 2274123 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Br:12])=[CH:4][CH:3]=1.[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O)=[O:14].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:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:13]=[O:14])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 665211,4-DibromonaphthaleneHCID 2921892-Formylphenylboronic acid

Product 1

HCID 596227241-Bromo-4-(2-formylphenyl)naphthaleneYield 67.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Under the atmosphere of argon, 230 g of 1,4-dibromonaphthalene, 121 g of 2-formylphenylboronic acid and 18.5 g of tetrakis(triphenylphosphine)palladium(0) were placed in a flask. To the resulting mixture, 2.4 L of dimethoxyethane (DME) and 1.2 L of an aqueous 2M sodium carbonate solution were added, followed by stirring under reflux for 8 hours. After cooling to the room temperature, an aqueous phase was removed, and an organic phase was washed with water and saturated saline, and dried with magnesium sulfate. After filtering off magnesium sulfate, the organic phase was concentrated. The residues were purified by silica gel column chromatography, whereby 170 g (yield 67%) of 1-bromo-4-(2-formylphenyl)naphthalene as an intended product was obtained.

Workup

  1. temperatureunder reflux for 8 hours
  2. customan aqueous phase was removed
  3. washan organic phase was washed with water and saturated saline
  4. dry with materialdried with magnesium sulfate
  5. filtrationAfter filtering off magnesium sulfate
  6. concentrationthe organic phase was concentrated

Sources & evidence

ORD record
ord-d8e547dffc4e4cc8bb241974f7c092a4
Source dataset
uspto-grants-2015_09
Patent number
US09126943B2

Reaction notes

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