Propionyl chloride → 4-(3-Bromopropylthio)phenylpropan-1-one

HRID 1722837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1722837
[Br:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:12](Cl)(=[O:15])[CH2:13][CH3:14].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 62324Propionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 70618473-Bromopropyl phenyl sulfide

Produkt 1

HCID 146502814-(3-Bromopropylthio)phenylpropan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of thioether from Example 1, (460 g, 2 moles) and propionyl chloride (202 g, 2.2 moles) in dichloromethane (8 L) at -15° C. was added in portions of approximately 30 g over 1 hour, aluminum chloride (320 g, 2.4 moles). After two hours at -15° C. the reaction mixture was quenched with ice until it became colorless. 1N HCl (2 L) was added and the reaction mixture was stirred until two clear phases were obtained (approximately 30 minutes). The organic layer was siphoned off and dried (Na2SO4). Evaporation afforded an oil which crystallized upon addition of hexane (2 L) and cooling in ice water bath; yield 470 g, m.p. 40°-41° C.

Aufarbeitung

  1. customAfter two hours at -15° C. the reaction mixture was quenched with ice until it
  2. addition1N HCl (2 L) was added
  3. customwere obtained (approximately 30 minutes)
  4. dry with materialdried (Na2SO4)
  5. customEvaporation
  6. customafforded an oil which
  7. customcrystallized upon addition of hexane (2 L)
  8. temperaturecooling in ice water bath

Quellen und Nachweise

ORD-Eintrag
ord-9c0f3f7046344989b041d75962298cf3
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04857659

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