Bromine → 3-Bromo-2-hydroxy-5-methoxybenzaldehyde

HRID 535681

Reaktionsgleichung

Reaktionsgleichung von HRID 535681
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])(=O)C.[Na+].[Br:17]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C>[Br:17][C:9]1[C:2]([OH:1])=[C:3]([CH:6]=[C:7]([O:10][CH3:11])[CH:8]=1)[CH:4]=[O:5]

Komponenten

6

Edukt 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 956952-Hydroxy-5-methoxybenzaldehydeHCID 517045Sodium Acetate

Produkt 1

HCID 7358183-Bromo-2-hydroxy-5-methoxybenzaldehydeAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To 2-hydroxy-5-methoxybenzaldehyde (4.1 mL, 32.86 mmol) in acetic acid (150 mL) were added sodium acetate (4.0 g, 49.3 mmol) and bromine (2.2 mL, 42.7 mmol) and the mixture was stirred at rt for 2 h. Aqueous sodium thiosulfate was added and the mixture was concentrated by rotary evaporation. The solid was dissolved in dichloromethane and washed with water. The organic phase was separated, dried over MgSO4, filtered and the solvent removed by rotary evaporation. The solid residue was recrystallized from ethanol to yield 3-bromo-2-hydroxy-5-methoxybenzaldehyde (4.55 g, 60%).

Aufarbeitung

  1. concentrationthe mixture was concentrated by rotary evaporation
  2. dissolutionThe solid was dissolved in dichloromethane
  3. washwashed with water
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed by rotary evaporation
  8. customThe solid residue was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-8c00af4ab9564cd780c098b2589daae7
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859534B2

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