4-Bromophenol → Ethyl 1-((4-bromophenoxy)methyl)cyclobutanecarboxylate

HRID 873720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 873720
CS([O:5][CH2:6][C:7]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9][CH2:8]1)(=O)=O.[Br:16][C:17]1[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([O:5][CH2:6][C:7]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9][CH2:8]2)=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 78084-BromophenolHCID 10796Cesium carbonateHCID 86724246Ethyl 1-{[(methylsulfonyl)oxy]methyl}cyclobutanecarboxylate

Produkt 1

HCID 86724262Ethyl 1-((4-bromophenoxy)methyl)cyclobutanecarboxylateAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

The mixture of ethyl 1-{[(methylsulfonyl)oxy]methyl}cyclobutanecarboxylate (1.50 g, 6.3 mmol), 4-bromophenol (1.2 g, 7.0 mmol), and caesium carbonate (4.13 g, 7.0 mmol) in DMF (15 ml) was stirred for 6 hours at 135° C. After dilution with EtOAc and H2O, the organic layer was washed with H2O, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (hexane:EtOAc=100:0-70:30) to give ethyl 1-[(4-bromophenoxy)methyl]cyclobutanecarboxylate (919 mg).

Aufarbeitung

  1. washAfter dilution with EtOAc and H2O, the organic layer was washed with H2O
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (hexane:EtOAc=100:0-70:30)

Quellen und Nachweise

ORD-Eintrag
ord-98fb229585bf4e17a00a4c0259845591
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975415B2

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