Methanol → Methyl 4-bromocinnamate

HRID 718683

Reaktionsgleichung

Reaktionsgleichung von HRID 718683
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.S(Cl)(Cl)(=O)=O.[CH3:18]O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:18])=[O:11])=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24648Sulfuryl chlorideHCID 737158(2E)-3-(4-bromophenyl)prop-2-enoic acid

Produkt 1

HCID 816774Methyl 4-bromocinnamate

Versuchsvorschrift

To a stirred solution of (2E)-3-(4-bromophenyl)prop-2-enoic acid (4.5 g, 0.020 mol) in MeOH (20 mL), sulfuryl dichloride (2.7 g, 0.023 mol) was added dropwise at 0° C. The resulting solution was heated to reflux for 1 h. The reaction mixture was allowed to cool to rt and concentrated to dryness under reduced pressure to yield a residue, which was subjected to flash column chromatography on silica gel (5-10% EtOAc/petroleum ether) to afford compound 66c as a colorless oil. Mass Spectrum (GCMS, ESI pos.): Calcd. for C10H9BrO2: 241.1 (M). found: 241.0.

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 1 h
  3. concentrationconcentrated to dryness under reduced pressure
  4. customto yield a residue, which

Quellen und Nachweise

ORD-Eintrag
ord-350318ee0faa4945acaea905790fa0d4
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193736B2

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