Isovanillin → 2-Bromoisovanillin

HRID 2427848Notes

Reaction equation

HRID 2427848 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].C([O-])(=O)C.[Na+].[Br:17]Br>C(O)(=O)C.[Cl-].[Na+].O.[Fe]>[Br:17][C:3]1[C:2]([OH:1])=[C:9]([O:10][CH3:11])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

7

Reactant 3

HCID 12127IsovanillinHCID 24408BromineHCID 517045Sodium Acetate

Product 1

HCID 2240112-Bromoisovanillin

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
15 °C

Procedure

3-Hydroxy-4-methoxy-benzaldehyde (20.0 g, 131.4 mmoles) and sodium acetate (23.7 g, 289.2 mmoles) are suspended in acetic acid (650 mL). Iron powder (513.8 mg, 9.2 mmoles) is added and the resulting suspension is cooled to approximately 15° C. A solution of bromine (23.1 g, 144.6 mmoles) in acetic acid (130 mL) is slowly (over 1 hour) dropped into the reaction mixture, keeping temperature at approximately 15° C. The reaction is left at room temperature for 30 minutes. The crude is poured in 780 mL of brine; the desired compound is filtered-off from the mother liquor and washed, sequentially, with brine and water. The product is dried under vacuum overnight to afford a white solid (26.6 g), which is used in the next step without further purification.

Workup

  1. custom(over 1 hour)
  2. additiondropped into the reaction mixture
  3. customat approximately 15° C

Sources & evidence

ORD record
ord-5cadeb8dd29a46f7a65ca1344628949f
Source dataset
uspto-grants-2011_06
Patent number
US07968724B2

Reaction notes

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