2-(Benzyloxy)-5-bromobenzaldehyde → (2-(Benzyloxy)-5-bromophenyl)methanol

HRID 392917

Reaktionsgleichung

Reaktionsgleichung von HRID 392917
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:12]=1[CH:13]=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:12]=1[CH2:13][OH:14])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

4

Edukt 2

HCID 7330872-(Benzyloxy)-5-bromobenzaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 897136(2-(Benzyloxy)-5-bromophenyl)methanolAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (339 mg, 8.93 mmol) was added to a solution of 2-benzyloxy-5-bromo-benzaldehyde (2.6 g, 8.93 mmol) in anhydrous ethanol (20 mL) at 0° C. The reaction was allowed to warm to room temperature and, after 3 hours, the mixture was concentrated and the residue was dissolved in ethyl acetate (50 mL) and washed with water (1×25 mL), 1N HCl solution (1×25 mL) and brine (1×25 mL). The solution was dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (8% ethyl acetate/hexane) to afford 2.58 g of the title compound as a colorless oil (98%).

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  3. washwashed with water (1×25 mL), 1N HCl solution (1×25 mL) and brine (1×25 mL)
  4. dry with materialThe solution was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (8% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8da6b060110d420c939cce3163a83cf8
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06803457B1

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