3',4',5'-Trimethoxyacetophenone → 2-Bromo-1-(3,4,5-trimethoxyphenyl)ethanone

HRID 618080

Reaktionsgleichung

Reaktionsgleichung von HRID 618080
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C1CNC(=O)C1.[Br:22][Br-]Br>O1CCCC1>[Br:22][CH2:14][C:13]([C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:15]

Komponenten

3

Edukt 1

HCID 143453',4',5'-Trimethoxyacetophenone

Produkt 1

HCID 36857322-Bromo-1-(3,4,5-trimethoxyphenyl)ethanoneAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

3',4',5'-Trimethoxyacetophenone (15.0 g) and pyrrolidone hydrotribromide (35.39 g) were dissolved in tetrahydrofuran (225 ml), followed by stirring at 40° C. for one hour. The reaction solution was cooled to room temperature, precipitated crystals were filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and the obtained crude crystals were washed with hexane (100 ml) to give 2-bromo-3',4',5'-trimethoxyacetophenone (Compound XIa, 12.20 g).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. customprecipitated crystals
  3. filtrationwere filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. customthe obtained crude crystals
  7. washwere washed with hexane (100 ml)

Quellen und Nachweise

ORD-Eintrag
ord-0b230950158c4ee38d667994500d094c
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952355

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