Water → 2-Amino-5-bromobenzenemethanol

HRID 44189

Reaktionsgleichung

Reaktionsgleichung von HRID 44189
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:9]=1[C:10](OC)=[O:11].O.[OH-].[Na+]>C1COCC1>[NH2:7][C:8]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:9]=1[CH2:10][OH:11]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 736224Methyl 2-amino-5-bromobenzoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 110308742-Amino-5-bromobenzenemethanolAusbeute 59,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of lithium aluminium hydride (0.33 g, 8.7 mmol) in THF (10 ml) was added a solution of methyl 2-amino-5-bromobenzoate (2.0 g, 8.7 mmol) in 20 ml THF at 0° C. under nitrogen. Then stirring was continued for 2 h. 0.64 ml water, 2 M solution of sodium hydroxide (0.64 ml) and again 1.28 ml water were added before the resulting mixture was filtered through celite. Evaporation of the solvent and purification of the crude product by flash chromatography on silica gel (dichloromethane/ethyl acetate, 2/1) yielded (2-amino-5-bromophenyl)methanol (1.0 g, 5.2 mmol, 59%) as off-white solid.

Aufarbeitung

  1. filtrationwas filtered through celite
  2. customEvaporation of the solvent and purification of the crude product by flash chromatography on silica gel (dichloromethane/ethyl acetate, 2/1)

Quellen und Nachweise

ORD-Eintrag
ord-eac0c260257f408f86bcc379c762a4e5
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541404B2

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