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

HRID 594866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 594866
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-07cd15ed267d417abc6ffb36670e8099
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242973B2

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