Ethanol → Ethyl 2-(4-bromophenyl)acetate

HRID 1362

Reaktionsgleichung

Reaktionsgleichung von HRID 1362
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.OS(O)(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH2:23](O)[CH3:24]>>[CH2:23]([O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH3:24]

Komponenten

5

Edukt 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 74654Benzeneacetic acid, 4-bromo-

Produkt 1

HCID 7020609Ethyl 2-(4-bromophenyl)acetate

Versuchsvorschrift

A solution of 43 g (200 mmol) of 4-bromophenylacetic acid and 0.2 g of conc. H2SO4 in 470 ml of ethanol was refluxed for 16 hours. The reaction mixture was cooled to ambient temperature, stirred with 6 g of solid K2CO3 for 30 minutes and then filtered. The filtrate was concentrated in vacuo, diluted with Et2O (200 ml), washed with 10% aqueous NaHCO3 (10 ml) and brine (10 ml), dried over MgSO4 and concentrated in vacuo to give the title compound as a colorless oil. PMR (CDCl3): δ 1.25 (3H, t, J=7.0 Hz), 3.56 (2H, s), 4.15 (2H, q, J=7.0 Hz), 7.16 (2H, d, J=8.4 Hz), 7.45 (2H, d, J=8.4 Hz).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. additiondiluted with Et2O (200 ml)
  4. washwashed with 10% aqueous NaHCO3 (10 ml) and brine (10 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-40f1c896966e44febe91ff5b043dfe79
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723666

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