Triethylamine → 2-(Benzylsulfanyl)ethyl 2-bromopropanoate

HRID 542668

Reaktionsgleichung

Reaktionsgleichung von HRID 542668
[Br:1][CH:2]([CH3:6])[C:3](Br)=[O:4].C(N(CC)CC)C.[CH2:14]([S:21][CH2:22][CH2:23][OH:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[Br:1][CH:2]([CH3:6])[C:3]([O:24][CH2:23][CH2:22][S:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 774862-(Benzylthio)ethanolHCID 79047Propanoyl bromide, 2-bromo-

Produkt 1

HCID 133096302-(Benzylsulfanyl)ethyl 2-bromopropanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A solution of 21.6 g of 2-bromopropionyl bromide in 30 ml of toluene was added dropwise to a solution of 10.1 g of triethylamine and 16.8 g of 2-benzylthioethanol in 150 ml of toluene at room temperature whilst stirring. After the addition was completed, the reaction mixture was stirred for a further 2 hours at room temperature. The mixture was then washed successively with 1% strength by weight aqueous solution of sodium hydroxide and water. After drying the organic phase over anhydrous sodium sulphate, the toluene was distilled off under reduced pressure, and the end product of 2-benzylthioethyl 2-bromopropionate was obtained in a yield of 28.8 g as a colorless product.

Aufarbeitung

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred for a further 2 hours at room temperature
  3. washThe mixture was then washed successively with 1% strength by weight aqueous solution of sodium hydroxide and water
  4. dry with materialAfter drying the organic phase over anhydrous sodium sulphate
  5. distillationthe toluene was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-605d5b05a507480e92505a7c49a15763
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659370

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