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

HRID 31557

반응식

HRID 31557 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-abf460ed81be43d187535088aca79c21
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425653B2

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