Water → 2-Bromo-5-methoxybenzaldehyde

HRID 1898765Notes

Reaction equation

HRID 1898765 reaction equation
[CH:1](=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.C([O-])(=O)C.[Na+].[Br:16]Br.O>C(O)(=O)C>[Br:16][C:7]1[CH:6]=[CH:5][C:4]([O:8][CH3:9])=[CH:3][C:2]=1[CH:1]=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 115693-MethoxybenzaldehydeHCID 24408BromineHCID 517045Sodium Acetate

Product 1

HCID 3444802-Bromo-5-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of m-anisaldehyde (25.2 g) and anhydrous sodium acetate (37.6 g) in acetic acid (150 ml) is added bromine (30.8 g) and the resulting solution stirred 45° C. overnight, then at room temperature for about 4 hours. The reaction mixture is poured into water (300 ml), stirred for 15 minutes, then filtered and the solid residue dissolved in toluene. The toluene solution is washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is recrystallized from hexanes to give the desired product.

Workup

  1. waitat room temperature for about 4 hours
  2. stirringstirred for 15 minutes
  3. filtrationfiltered
  4. dissolutionthe solid residue dissolved in toluene
  5. washThe toluene solution is washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is recrystallized from hexanes

Sources & evidence

ORD record
ord-92230b7a35c94cb3a30c2630c9b9a042
Source dataset
uspto-grants-1996_11
Patent number
US05571506

Reaction notes

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