Cesium carbonate → 3-[4-(2-Bromo-phenoxy)-2-methyl-phenyl]-propionic acid methyl ester

HRID 1822276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1822276
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH3:13].[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1I.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C>CN1CCCC1=O.[Cu]Cl>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[Br:15])=[CH:8][C:7]=1[CH3:13]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 114151-Bromo-2-iodobenzeneHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 13551833Methyl 3-(4-Hydroxy-2-methylphenyl)propanoate

Produkt 1

HCID 578942223-[4-(2-Bromo-phenoxy)-2-methyl-phenyl]-propionic acid methyl esterAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester (2.0 g, 10.3 mmol), 1-bromo-2-iodobenzene (8.74 g, 30.9 mmol), cesium carbonate (4.03 g, 12.4 mmol), copper (I) chloride (0.51 g, 5.15 mmol) and 2,2,6,6-tetramethyl-3,5-heptanedione (0.47 g, 2.55 mmol) in 1-methyl-2-pyrrolidinone (20 mL) is heated to 120° C. for 10 hours under N2. The reaction is cooled and quenched with 1 N HCl. The mixture is then diluted with Et2O and extracted with water. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 9/1 hexanes/ethyl acetate to afford 1.09 g (30%) of the title compound. Rf=0.34 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3).

Aufarbeitung

  1. temperatureThe reaction is cooled
  2. customquenched with 1 N HCl
  3. additionThe mixture is then diluted with Et2O
  4. extractionextracted with water
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. customthe solvent is removed in vacuo
  7. customto afford crude product that
  8. customis absorbed on silica gel
  9. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8d54c1ccd4c44513bcfcf04f87f8fcd1
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608639B2

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