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

HRID 2405458Notes

Reaction equation

HRID 2405458 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%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A flask was charged with 230 g of 1,4-dibromonaphthalene, 121 g of 2-formylphenylboronic acid, and 18.5 g of tetrakis(triphenylphosphine)palladium(0) in an argon atmosphere. After the addition of 2.4 L of dimethoxyethane (DME) and 1.2 L of a 2 M sodium carbonate aqueous solution, the mixture was heat refluxed with stirring for 8 hours. The mixture was then cooled to room temperature. After removing the aqueous phase, the organic phase was washed with water and a saturated sodium chloride solution, and dried over magnesium sulfate. After removing magnesium sulfate by filtration, the organic phase was concentrated. The residue was purified by silica gel column chromatography to obtain 170 g of the target 1-bromo-4-(2-formylphenyl)naphthalene (yield: 67%).

Workup

  1. temperaturethe mixture was heat
  2. temperaturerefluxed
  3. customAfter removing the aqueous phase
  4. washthe organic phase was washed with water
  5. dry with materiala saturated sodium chloride solution, and dried over magnesium sulfate
  6. customAfter removing magnesium sulfate
  7. filtrationby filtration
  8. concentrationthe organic phase was concentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d22be38e2aaf4630b048e89953a565bd
Source dataset
uspto-grants-2014_08
Patent number
US08803420B2

Reaction notes

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