Potassium Carbonate → 4-Chloro-3-(4-methoxyphenyl)benzenecarboxaldehyde

HRID 460127ノート

反応式

HRID 460127 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH:16]=[O:17].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(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>[Cl:21][C:20]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][C:13]=1[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 140498093-Bromo-4-chlorobenzaldehyde

生成物 1

HCID 223913894-Chloro-3-(4-methoxyphenyl)benzenecarboxaldehyde収率 62.6%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 21863594Toluene ethanol溶媒

実験手順

To a degassed solution of 4-methoxybenzeneboronic acid (1.51 g, 10 mmol), 3-bromo-4-chlorobenzaldehyde (2 g, 9.13 mmol), and potassium carbonate (3.13 g, 22.8 mmol) in toluene/ethanol 2/1, (60 mL), Pd(PPh3)4 (130 mg, 1 mol %) is added and the mixture is degassed for further 5 minutes. The mixture is then refluxed for 2 days. The mixture was partitioned between ethyl acetate and water and extracted. The organic solvent was dried over sodium sulphate, removed under reduced pressure, and the residue purified by column chromatography (heptane/ethyl acetate 19/1 to afford 1.41 g of product.

後処理

  1. customthe mixture is degassed for further 5 minutes
  2. temperatureThe mixture is then refluxed for 2 days
  3. customThe mixture was partitioned between ethyl acetate and water
  4. extractionextracted
  5. dry with materialThe organic solvent was dried over sodium sulphate
  6. customremoved under reduced pressure
  7. customthe residue purified by column chromatography (heptane/ethyl acetate 19/1

出典と根拠

ORDレコード
ord-df9deeee344f4fa0bff9bd2ffb42385f
出典データセット
uspto-grants-2007_03
特許番号
US07196102B2

反応ノート

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