Water → 5-Bromovanillin

HRID 2410932Notes

Reaction equation

HRID 2410932 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[Br:12]Br.O>CO>[Br:12][C:10]1[C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=[C:3]([CH:11]=1)[CH:2]=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 1183VanillinHCID 24408Bromine

Product 1

HCID 180995-BromovanillinYield 92.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of vanillin (7.6 g, 50 mmol) in MeOH (60 mL) was added dropwise Br2 (2.8 mL, 50 mmol) over a 2 h period at 0° C. The mixture was warm to room temperature for another 1 h. Then cooling to 0° C., water (25 mL) was poured over a 20 min period and resulted in the precipitation of white solid. The mixture was stirred for further 15 min. The precipitate was filtered, washed with ice water and dried to give 10.7 g of white solid. Spectrum analysis verified the compound is 5-Br-vanillin.

Workup

  1. temperatureThen cooling to 0° C.
  2. customresulted in the precipitation of white solid
  3. filtrationThe precipitate was filtered
  4. washwashed with ice water
  5. customdried

Sources & evidence

ORD record
ord-ecb6e8e0b4ce483ab8ea8803b6c7eb45
Source dataset
uspto-grants-2014_08
Patent number
US08816129B2

Reaction notes

Loading…