Potassium Carbonate → 6-(Cyclopropylmethoxy)-4′-methoxy[1,1′-biphenyl]-3-carboxaldehyde

HRID 460139노트

반응식

HRID 460139 반응식
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH:12]1[CH2:14][CH2:13]1)[CH:5]=[O:6].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.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>[CH:12]1([CH2:11][O:10][C:9]2[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=2[C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 22391279HCID 22391279, 화합물

생성물 1

HCID 223915076-(Cyclopropylmethoxy)-4′-methoxy[1,1′-biphenyl]-3-carboxaldehyde수율 89.7%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 21863594Toluene ethanol용매

실험 절차

To a degassed solution of 3-bromo-4-cyclopropylmethoxybenzaldehyde (1.53 g, 6 mmol), 4-methoxybenzeneboronic acid (1.22 g, 8 mmol) and potassium carbonate (2.74 g, 20 mmol) in toluene/ethanol 2/1 (40 mL), Pd(PPh3)4 (100 mg) was added and the mixture was degassed for further 5 minutes. The mixture was then refluxed for 12 hours. The solid is filtered off, and the solvent partitioned between ethyl acetate and water and extracted. The organic solvent was removed under reduced pressure, dried over sodium sulphate and purified by column chromatography on silica (hexane/ethyl acetate 8/2) to afford 1.52 g of product.

후처리

  1. customthe mixture was degassed for further 5 minutes
  2. temperatureThe mixture was then refluxed for 12 hours
  3. filtrationThe solid is filtered off
  4. customthe solvent partitioned between ethyl acetate and water
  5. extractionextracted
  6. customThe organic solvent was removed under reduced pressure
  7. dry with materialdried over sodium sulphate
  8. custompurified by column chromatography on silica (hexane/ethyl acetate 8/2)

출처 및 근거

ORD 기록
ord-fd3db669104e4f38bbfbf80bced03d0c
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196102B2

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