Water → Methyl 2-(bromomethyl)-3-fluorobenzoate

HRID 2301126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2301126
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[CH3:11].[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.O>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[CH2:11][Br:13]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 21752566Methyl 3-fluoro-2-methylbenzoate

Produkt 1

HCID 19788116Methyl 2-(bromomethyl)-3-fluorobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5943Carbon TetrachlorideLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

3-Fluoro-2-methyl-benzoic acid methyl ester (4.3 g, 26 mmol), N-bromosuccinimide (5.0 g, 28 mmol) and AIBN (2,2′-azobisisobutyronitril) (420 mg, 2.6 mmol) were stirred at 80° C. for 10 hours in carbon tetrachloride (45 ml). The reaction solution was mixed with water and chloroform, washed with saturated sodium bicarbonate aqueous solution and saturated brine and then dried with anhydrous magnesium sulfate. The solvent was removed by evaporation from the extract under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 5.1 g (21 mmol, 81% in yield) of the title compound.

Aufarbeitung

  1. washwashed with saturated sodium bicarbonate aqueous solution and saturated brine
  2. dry with materialdried with anhydrous magnesium sulfate
  3. customThe solvent was removed by evaporation from the
  4. extractionextract under a reduced pressure
  5. customthe thus obtained material was separated
  6. custompurified by a silica gel column chromatography
  7. customto obtain

Quellen und Nachweise

ORD-Eintrag
ord-acb67e1114d24c75a6db98c93fadaee7
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498251B1

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