Ammonium Chloride → (4-Bromo-3-methylphenyl)methanol

HRID 250858

Reaktionsgleichung

Reaktionsgleichung von HRID 250858
[BH4-].[Li+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[Br:14])[C:7](OC)=[O:8].[Cl-].[NH4+]>O1CCCC1>[Br:14][C:13]1[CH:12]=[CH:11][C:6]([CH2:7][OH:8])=[CH:5][C:4]=1[CH3:3]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 3294148Methyl 4-bromo-3-methylbenzoateHCID 4148881Lithium borohydride

Produkt 1

HCID 10987288(4-Bromo-3-methylphenyl)methanolAusbeute 104,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

284 mg (12.9 mmol, 3 eq) of lithium borohydride are added to a solution of 1.0 g (4.3 mmol, 1 eq) of methyl 3-methyl-4-bromobenzoate in 10 ml of tetrahydrofuran. The reaction mixture is stirred at 60° C. for 12 hours. The reaction medium is hydrolyzed with ammonium chloride solution and extracted with ethyl acetate. The organic phases are combined, washed with sodium chloride solution and dried over sodium sulfate. 900 mg of (4-bromo-3-methylphenyl)methanol are obtained in oil form and used in the following reaction without further purification.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed with sodium chloride solution
  3. dry with materialdried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-248d93701dd240b08ba4e4ee8037fabb
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863332B2

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