Vanillin → 5-Bromovanillin

HRID 639029Notes

Reaction equation

HRID 639029 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>C(O)(=O)C>[Br:12][C:10]1[CH:11]=[C:3]([CH:4]=[C:5]([O:6][CH3:7])[C:8]=1[OH:9])[CH:2]=[O:1]

Participants

4

Reactant 2

HCID 1183VanillinHCID 24408Bromine

Product 1

HCID 180995-BromovanillinYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

To a solution of vanillin (30.40 g, 0.20 mol) in glacial acetic acid (200 mL) was added bromine (46.79 g, 0.29 mol) in glacial acetic acid (20 mL) at 10° over a period of 1 h. Additional acetic acid (100 mL) was added to the thickening mixture and the reaction was stirred for 24 h at ambient temperature. The reaction was diluted with ice/water (300 mL); the precipitate was filtered and washed well with water. A light beige solid (40.69 g, 89%) was obtained after vacuum drying: MS (ES) m/z 230.0. (M+H)+.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed well with water

Sources & evidence

ORD record
ord-82e0b4b30b814700b90768ff339039aa
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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