Sodium Carbonate → 2-(6-Methyl-2-naphthyl)benzaldehyde

HRID 31557

Reaction equation

HRID 31557 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[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+]>C(COC)OC>[CH3:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH:13]=[O:14])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 6405922-Bromo-6-methylnaphthalene

Product 1

HCID 862261722-(6-Methyl-2-naphthyl)benzaldehydeYield 91%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Under an atmospheric argon gas flow, 2-bromo-6-methylnaphthalene in an amount of 6.6 g (30 mmol), 2-formylphenylboronic acid in an amount of 5.4 g (36 mmol), (tetrakistriphenylphosphine)palladium in an amount of 0.7 g (0.6 mmol), 2N sodium carbonate aqueous solution in an amount of 45 milliliter and dimethoxyethane in an amount of 90 milliliter were placed into a three neck flask with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was refluxed under heating for 8 hours. After the reaction terminated, adding water in an amount of 100 milliliter into the reacted solution, an organic layer was separated and washed with the use of sodium chloride solution, followed by drying with the use of magnesium sulfate. After removing the solvent by distillation by means of a rotary evaporator, the resultant crude product was refined by means of column chromatography (silicagel, hexane/dichloromethane=60/40), and as a result, 6.7 g of aimed compound (white crystal) was obtained (yield: 91%).

Workup

  1. temperatureunder heating for 8 hours
  2. customAfter the reaction terminated
  3. additionadding water in an amount of 100 milliliter into the reacted solution
  4. customan organic layer was separated
  5. washwashed with the use of sodium chloride solution
  6. dry with materialby drying with the use of magnesium sulfate
  7. customAfter removing the solvent
  8. distillationby distillation
  9. customby means of a rotary evaporator

Sources & evidence

ORD record
ord-abf460ed81be43d187535088aca79c21
Source dataset
uspto-grants-2008_09
Patent number
US07425653B2

Linked notes

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