Water → [3-Bromo-5-(trifluoromethyl)phenyl]methanol

HRID 355369

Reaktionsgleichung

Reaktionsgleichung von HRID 355369
[BH4-].[Li+].[Br:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[C:7](OC)=[O:8].O>CCOCC.[NH4+].[Cl-]>[Br:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=1)[CH2:7][OH:8]

Komponenten

6

Edukt 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 18942156Methyl 3-bromo-5-(trifluoromethyl)benzoate

Produkt 1

HCID 29919767[3-Bromo-5-(trifluoromethyl)phenyl]methanolAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

Lithium borohydride (22 0mg) was added in a single portion to a stirred solution of methyl 3-bromo-5-(trifluoromethyl)benzoate (2.46 g) in ether (60 ml) containing water (156 ml). The resulting solution was stirred for 4 hours at room temperature, at which point the reaction mixture was diluted with saturated aqueous NH4Cl solution (50 ml). The organic layers were separated, dried over MgSO4, filtered and the solvent removed under reduced pressure to give 3-bromo-5-(trifluoromethyl)benzyl alcohol as a clear oil (2.1 g).1H NMR (360 MHz,CDCl3) δ 1.83 (1H, br s), 4.76 (2H,s), 7.47 (1H, s), 7.56 (1H, s), 7. 68 (1H, s).

Aufarbeitung

  1. customThe organic layers were separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-917a6a113bd240b086d0b393ab3ee70e
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05830892

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