Sodium borohydride → 3-Bromo-2-(hydroxymethyl)phenol

HRID 1473913

Reaktionsgleichung

Reaktionsgleichung von HRID 1473913
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[C:3]([CH2:4][OH:5])=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 119547682-Bromo-6-hydroxybenzaldehyde

Produkt 1

HCID 861260253-Bromo-2-(hydroxymethyl)phenolAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-6-hydroxybenzaldehyde (3.8 g, 18.91 mmol, 1 eq.) in a mixture of THF and MeOH (4/1, 25 mL) was added NaBH4 (1.4 g, 37.81 mmol, 1.5 eq.) at rt portion-wise. Upon the completion of addition, the mixture was continued to stir at rt for 30 min. The mixture was quenched with HCl (4 N) and extracted with EtOAC twice. The combined organic layer was dried over Na2SO4, concentrated, and purified on silica gel using 25% EtOAc/hexanes as eluent to give 3-bromo-2-(hydroxymethyl)phenol (2.3 g, 60%) as a colorless oil.

Aufarbeitung

  1. additionUpon the completion of addition
  2. customThe mixture was quenched with HCl (4 N)
  3. extractionextracted with EtOAC twice
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified on silica gel using 25% EtOAc/hexanes as eluent

Quellen und Nachweise

ORD-Eintrag
ord-b6a2b4f73fb24d26b0093fbe1e9f338d
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018210B2

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