Hydrogen Bromide → Methyl 5-(bromomethyl)-4-methylthiophene-2-carboxylate

HRID 69086

Reaktionsgleichung

Reaktionsgleichung von HRID 69086
[CH3:1][C:2]1[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[S:5][CH:6]=1.[BrH:11].OS(O)(=O)=O.[CH2:17]=O>ClCCl.O.[Zn+2].[Br-].[Br-]>[Br:11][CH2:17][C:6]1[S:5][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:3][C:2]=1[CH3:1]

Komponenten

8

Edukt 4

HCID 260Hydrogen BromideHCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 2777593Methyl 4-methylthiophene-2-carboxylate

Produkt 1

HCID 67235212Methyl 5-(bromomethyl)-4-methylthiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10421208Zinc bromideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-methylthiophene-2-carboxylate (2.7 g, 6.4 mmol) in dichloromethane (20 mL) is added 48% aq. HBr (12 mL), H2SO4 (6 mL), ZnBr2 (5.4 g), and HCHO (2.2 mL, 37%) at 0-5° C. The mixture is stirred at room temperature for 16 hours. The solution is diluted with water, extracted with dichloromethane, washed with NaHCO3 solution, saturated brine solution, water, dried over sodium sulfate, and concentrated to give the title compound as an off white solid (3.5 g, 81%).

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washwashed with NaHCO3 solution, saturated brine solution, water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-75a3a1029acb46478cf275d50c0806ed
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822486B2

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