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

HRID 383853

Reaction equation

HRID 383853 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-61c8486805504bb5aeec8be56df7704d
Source dataset
uspto-grants-2013_02
Patent number
US08367676B2

Linked notes

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