Bromine → 2-Bromo-3-oxo-3-o-tolyl-propionic acid ethyl ester

HRID 474350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 474350
[Br:1]Br.[CH2:3]([O:5][C:6](=[O:17])[CH2:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])[CH3:4]>O1CCOCC1.COC(C)(C)C>[CH2:3]([O:5][C:6](=[O:17])[CH:7]([Br:1])[C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])[CH3:4]

Komponenten

5

Edukt 2

HCID 24408BromineHCID 2760276Ethyl 2-methyl-beta-oxobenzenepropanoate

Produkt 1

HCID 224373882-Bromo-3-oxo-3-o-tolyl-propionic acid ethyl esterAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 15413tert-Butyl methyl etherLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Bromine (1.65 g, 10.3 mmol, 1.03 equiv) was added drop-wise to a stirred solution of 3-oxo-3-o-tolyl-propionic acid ethyl ester (2.06 g, 10.0 mmol, 1.0 equiv) in 1,4-dioxane (25 mL) at ambient temperature. The mixture was stirred for 1 hour and then diluted with tert-butyl methyl ether (50 mL). The resultant solution was washed sequentially with water, aqueous potassium carbonate solution and saturated aqueous sodium chloride solution. The collected organic was dried over magnesium sulphate, filtered, and concentrated under vacuum to afford 2.74 g (96%) of 2-bromo-3-oxo-3-o-tolyl-propionic acid ethyl ester as a dark brown residue. 1H NMR (400 MHz, CDCl3) δ: 7.66 (d, 1H), 7.46-7.37 (m, 1H), 7.28 (m, 2H), 5.62 (s, 1H), 4.29-4.22 (q, 2H), 2.52 (s, 3H), 1.28-1.19 (t, 3H).

Aufarbeitung

  1. washThe resultant solution was washed sequentially with water, aqueous potassium carbonate solution and saturated aqueous sodium chloride solution
  2. dry with materialThe collected organic was dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-60e0ed2d14374d01938f396617b354bf
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637526B2

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