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

HRID 2422256
ノート
印刷プレビュー

反応式

HRID 2422256 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 2

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

生成物 1

HCID 230830313-(2-Methylnaphthalen-1-yl)benzaldehyde収率 65%

試薬・触媒・溶媒 6

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962
Water
溶媒
HCID 1140Toluene溶媒
HCID 8857Ethyl Acetate溶媒
HCID 10340Sodium Carbonate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-052080beb3114ebfaa9997b2d51d07d0
出典データセット
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07960369B2

反応ノート

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