Dimethyl Sulfate → 1-Bromo-3-[3-(2-methoxy-ethyl)-cyclobutyl]-benzene

HRID 2240965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240965
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:11][CH:10]([CH2:12][CH2:13][OH:14])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[CH3:17]OS(OC)(=O)=O>C(OCC)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[CH2:9][CH:10]([CH2:12][CH2:13][O:14][CH3:17])[CH2:11]2)[CH:3]=1

Komponenten

6

Edukt 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 593052992-[3-(3-Bromo-phenyl)-cyclobutyl]-ethanol

Produkt 1

HCID 593053151-Bromo-3-[3-(2-methoxy-ethyl)-cyclobutyl]-benzeneAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

2-[3-(3-Bromo-phenyl)-cyclobutyl]-ethanol (0.500 gm, 1.96 mmol) was dissolved in diethylether (7 mL) and combined with tetrabutylammonium iodide (75 mg, 0.203 mmol), an aqueous solution of sodium hydroxide (5 gm, 50% wt/wt, 62.5 mmol) and dimethylsulfate (0.50 ml, 5.27 mmol). The mixture was stirred overnight at ambient temperature then diluted with diethyl ether and decanted. The supernatant was concentrated onto silica and purified by column chromatography (25% diethylether in hexanes) to afford 389 mg of an oil (74%). This material was used in next step without further characterization.

Aufarbeitung

  1. customdecanted
  2. concentrationThe supernatant was concentrated onto silica
  3. custompurified by column chromatography (25% diethylether in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b6f9e42fc9614c63ac949be046013eb5
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723368B2

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