Ethyl bromoacetate → 14738-27-3

HRID 458654

Reaktionsgleichung

Reaktionsgleichung von HRID 458654
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:11]([O:13][C:14](=[O:17])[CH2:15]Br)[CH3:12]>C1COCC1>[CH2:11]([O:13][C:14](=[O:17])[CH2:15][S:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[CH3:12]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 78114-MethylbenzenethiolHCID 24758Sodium hydride

Produkt 1

HCID 27149214738-27-3Ausbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 4-methylbenzenethiol (5 g, 40.25) in dry THF was added dropwise to a suspension of NaH (60% in mineral oil, 1.98 g, 48.30) in THF at room temperature and stirred for 30 min. under N2 atmosphere. Ethylbromoacetate (4.9 mL, 44.27) was added slowly to this solution and further stirred at room temperature for 3 h. The solvent was removed under vacuum. The residue was dissolved in dil. HCl and extracted by ethylacetate. The combined organic phase was washed successively with saturated NaHCO3 solution, water and brine then dried over Na2SO4. Evaporation of organic phase yielded 8.46 g (99%) colorless oil. 1H NMR (CDCl3): δ 1.22 (t, J=7.2 Hz, 3H), 2.32 (s, 3H), 3.57 (s, 2H), 4.14 (q, J=7.2 Hz, 2H), 7.11 (d, J=8.0 Hz, 2H), 7.33 (d, J=8.0 Hz, 2H). EIMS m/z 210 (M+1), 233 (M+23).

Aufarbeitung

  1. stirringfurther stirred at room temperature for 3 h
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in dil. HCl
  4. extractionextracted by ethylacetate
  5. washThe combined organic phase was washed successively with saturated NaHCO3 solution, water and brine
  6. dry with materialthen dried over Na2SO4
  7. customEvaporation of organic phase

Quellen und Nachweise

ORD-Eintrag
ord-1a23cb3f0c8f41c38ca4003189003af3
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192961B2

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