Iodine → 5-Bromo-4-formyl-2-methoxyphenyl acetate

HRID 1898759Notes

Reaction equation

HRID 1898759 reaction equation
[C:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:13][CH3:14])(=[O:3])[CH3:2].C([O-])(=O)C.[Na+].II.[Br:22]Br>C(O)(=O)C.O>[C:1]([O:4][C:5]1[CH:12]=[C:11]([Br:22])[C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:13][CH3:14])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 807IodineHCID 24408BromineHCID 61229Vanillin acetateHCID 517045Sodium Acetate

Product 1

HCID 2623485-Bromo-4-formyl-2-methoxyphenyl acetate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

To a mixture of 4-acetoxy-3-methoxybenzaldehyde (75.7 g), anhydrous sodium acetate (76 g) and iodine (0.8 g) in acetic acid (300 ml) is added bromine (21 ml). The mixture is warmed to 45° C. for about 1 hour, then stirred stirred at room temperature for 3 days, poured into water (700 ml) and filtered. The solid is dissolved in toluene and the solution washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is recrystallized twice from hexanes to give the desired product.

Workup

  1. stirringstirred at room temperature for 3 days
  2. filtrationfiltered
  3. dissolutionThe solid is dissolved in toluene
  4. washthe solution washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is recrystallized twice from hexanes

Sources & evidence

ORD record
ord-8a80e624349342b3b650619df4c01469
Source dataset
uspto-grants-1996_11
Patent number
US05571506

Reaction notes

Loading…