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

HRID 2113117ノート

反応式

HRID 2113117 の反応式
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

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 22391279HCID 22391279、化合物

生成物 1

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

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 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.

後処理

  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)

出典と根拠

ORDレコード
ord-78aba6adfc49485798c6201c9feafca7
出典データセット
uspto-grants-2009_04
特許番号
US07524873B2

反応ノート

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