Isovanillin → 2-Bromoisovanillin

HRID 850477Notes

Reaction equation

HRID 850477 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].O1CCOCC1.[Br:18]N1C(=O)CCC1=O>O>[Br:18][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

5

Reactant 3

HCID 12127IsovanillinHCID 312751,4-DioxaneHCID 67184N-bromobutanimide2×

Product 1

HCID 2240112-BromoisovanillinYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3-Hydroxy-4-methoxybenzaldehyde (200 g, 1.31 mol), dioxane (1000 ml) and water (400 ml) were mixed, and N-bromosuccinimide (245.7 g, 1.38 mol) was added over 10 minutes. After 60 and 70 minutes, N-bromosuccinimide was further added in an amount of 16.4 g (92.1 mmol) and 7.02 g (39.4 mmol), respectively, and the mixture was further stirred for 30 minutes. Water (1600 ml) was added, and the precipitated crystals were collected by filtration. The crystals were washed with water (1000 ml) to give 2-bromo-3-hydroxy-4-methoxybenzaldehyde (227.1 g, 74.8%) as pale-red crystals.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washThe crystals were washed with water (1000 ml)

Sources & evidence

ORD record
ord-dd25055b397c445a927ecfa7693a37cc
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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