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

HRID 584311

Reaktionsgleichung

Reaktionsgleichung von HRID 584311
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](O)=[O:6].B.C1COCC1.C1COCC1.O.[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[CH:9][C:10]=1[CH3:11]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 821303-Bromo-4-methylbenzoic acidHCID 2723981Borane;tetrahydrofuranHCID 21881883Oxolane--water (1/1)

Produkt 1

HCID 12947381(3-Bromo-4-methylphenyl)methanolAusbeute 102,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

15 g (70 mmol) of 3-bromo-4-methylbenzoic acid are placed in 150 ml of anhydrous THF in a round-bottomed flask and under a stream of nitrogen. 84 ml of 1M borane/THF are added dropwise and the reaction medium is stirred overnight at room temperature. A THF/water (50/50) solution is added slowly at 0° C. and the mixture is then poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. 14.4 g (100%) of the expected product are obtained in the form of a yellow oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2522160568b242deb5e70db5633e265d
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924400B2

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