N-bromobutanimide → (4-(Bromomethyl)phenyl)(cyclopropyl)methanone

HRID 413518

Reaktionsgleichung

Reaktionsgleichung von HRID 413518
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:13](C)C)=[CH:9][CH:8]=1)=[O:6].[Br:16]N1C(=O)CCC1=O>C(Cl)Cl>[Br:16][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]([CH:4]2[CH2:3][CH2:2]2)=[O:6])=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimide2×HCID 987444-Chloro-4'-isopropylbutyrophenone

Produkt 1

HCID 15512829(4-(Bromomethyl)phenyl)(cyclopropyl)methanoneAusbeute 165,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Dissolve 4-chloro-1-(4-isopropyl-phenyl)-butan-1-one (20 g, 124 mmol) and 2,2′-Azolons (2-methylpropionitrile) (0.5 g) in methylene chloride (100 mL) and cool to 5° C. Add a suspension of N-bromosuccinimide (12 g) in methylene chloride (50 mL) and irradiate with light (150 Watt lamp), maintaining the temperature at 5° C. After 2, 3 and 7 hour time periods, add additional N-bromosuccinimide (6 g, 6 g, 2.8 g) and continue stirring. After 7.5 hours, wash with water (200 mL) and with 0.4M sodium hydrogen carbonate (2×200 mL). Dry (Na2SO4), evaporate the solvent in vacuo and recrystallize (hexane) to give the title compound as a crystalline solid (26.7 g).

Aufarbeitung

  1. additionAdd
  2. customirradiate with light (150 Watt lamp)
  3. temperaturemaintaining the temperature at 5° C
  4. washwash with water (200 mL) and with 0.4M sodium hydrogen carbonate (2×200 mL)
  5. dry with materialDry (Na2SO4)
  6. customevaporate the solvent in vacuo
  7. customrecrystallize (hexane)

Quellen und Nachweise

ORD-Eintrag
ord-23872b868f0d4d37895250f4965f65f2
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566526B2

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