Water → Methyl 4-bromo-2-((methylthio)methyl)benzoate

HRID 2393013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393013
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12]Br)[CH:3]=1.[CH3:14][S-:15].[Na+].O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12][S:15][CH3:14])[CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Produkt 1

HCID 18978023Methyl 4-bromo-2-((methylthio)methyl)benzoateAusbeute 41,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of methyl 4-bromo-2-(bromomethyl)benzoate (12 g) and sodium thiomethoxide (2.5 g) in toluene was stirred at 100° C. for 2 hours. The mixture was then cooled, poured into water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried (anhydrous sodium sulphate) and evaporated to afford a brown oil which was purified by column chromatography on silica gel giving methyl 4-bromo-2-(methylsulphenylmethyl)benzoate (4.1 g) as white crystals, m.p. 79.3° C.

Aufarbeitung

  1. temperatureThe mixture was then cooled
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (anhydrous sodium sulphate)
  6. customevaporated
  7. customto afford a brown oil which
  8. customwas purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-18e7dd901f034741b338d2d81b937741
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05804532

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