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

HRID 1072230노트

반응식

HRID 1072230 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 223913894-Chloro-3-(4-methoxyphenyl)benzenecarboxaldehyde수율 62.6%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 21863594Toluene ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-80862a31e9374d0b946156e2b82f9975
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908935B2

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