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1-Bromo-2-methylnaphthalene → 3-(2-Methylnaphthalen-1-yl)benzaldehyde

HRID 2422256
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인쇄 미리보기

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HRID 2422256 반응식
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH3:12].[CH:13]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)=[O:14]>C(=O)([O-])[O-].[Na+].[Na+].C(O)C.C1(C)C=CC=CC=1.O.C(OCC)(=O)C.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>[CH3:12][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[C:19]1[CH:20]=[C:15]([CH:16]=[CH:17][CH:18]=1)[CH:13]=[O:14]
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참가 물질

9

반응물 2

HCID 757541-Bromo-2-methylnaphthaleneHCID 27343563-Formylphenylboronic acid

생성물 1

HCID 230830313-(2-Methylnaphthalen-1-yl)benzaldehyde수율 65%

시약·촉매·용매 6

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매
HCID 962
Water
용매
HCID 1140Toluene용매
HCID 8857Ethyl Acetate용매
HCID 10340Sodium Carbonate용매

반응 조건

온도
80 °C

실험 절차

1-Bromo-2-methylnaphthalene (3.32 g, 15.0 mmol) and (3-formylphenyl)boronic acid (2.13 g, 15.0 mmol) was dissolved in a mixture of 1 M sodium carbonate aqueous solution (30 mL), ethanol (15 mL) and toluene (30 mL) and, after argon substitution, tetrakis(triphenylphosphine)palladium (0) (0.867 g, 0.750 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 80° C. for 24 hrs. The reaction mixture was cooled, diluted with water and ethyl acetate, and the insoluble material was filtered through celite. The organic layer of the filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-20% ethyl acetate/hexane) to give the title compound (2.39 g, yield 65%) as a pale-yellow oil.

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe insoluble material was filtered through celite
  3. washThe organic layer of the filtrate was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-20% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-052080beb3114ebfaa9997b2d51d07d0
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960369B2

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