Bromine → 2,4-Pentanedione, 3-(phenylmethylene)-

HRID 1975714

Reaktionsgleichung

Reaktionsgleichung von HRID 1975714
[CH2:1]([CH:8]([C:12](=[O:14])[CH3:13])[C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrBr>ClCCl>[CH:1](=[C:8]([C:9](=[O:11])[CH3:10])[C:12](=[O:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24408BromineHCID 977572,4-Pentanedione, 3-benzyl-

Produkt 1

HCID 957822,4-Pentanedione, 3-(phenylmethylene)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution containing 6.3 g of 3-benzyl-2,4-pentanedione in 50 ml of dichloromethane was gradually added 5.3 g of bromine in 20 ml of dichloromethane under cooling (0°-5° C.). The solution was stirred for 10 min. at 0° C. and the solvent evaporated in vacuo. The residue was dissolved in 100 ml of pyridine and refluxed for 30 min. Pyridine was evaporated in vacuo, the residue was dissolved in dichloromethane and washed first with 6M hydrochloric acid and then with 2.6M NaOH. The solvent was evaporated and the residue distilled in vacuo. Bp 186°-188° C./16 mm, yield 1.2 g.

Aufarbeitung

  1. temperatureunder cooling (0°-5° C.)
  2. customthe solvent evaporated in vacuo
  3. dissolutionThe residue was dissolved in 100 ml of pyridine
  4. temperaturerefluxed for 30 min
  5. customPyridine was evaporated in vacuo
  6. dissolutionthe residue was dissolved in dichloromethane
  7. washwashed first with 6M hydrochloric acid
  8. customThe solvent was evaporated
  9. distillationthe residue distilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9ef2542a0bc54e89bad3bec9512d3871
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05288750

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