Isovanillin → 2-Bromoisovanillin

HRID 1293438Notes

Reaction equation

HRID 1293438 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.C([O-])(=O)C.[Na+].[Br:17]Br.S(=O)(O)[O-].[Na+]>C(O)(=O)C.[Fe]>[Br:17][C:4]1[C:5]([OH:6])=[C:7]([O:8][CH3:9])[CH:10]=[CH:11][C:3]=1[CH:2]=[O:1]

Participants

7

Reactant 4

HCID 12127IsovanillinHCID 24408BromineHCID 517045Sodium AcetateHCID 23665763Sodium Bisulfite

Product 1

HCID 2240112-BromoisovanillinYield 45.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

Isovanillin (5 gm, 0.033 mol) was dissolved in glacial acetic acid (30 ml). Anhydrous sodium acetate (5.4 gm) was added to the above solution followed by powdered iron (0.15 gm). The system was flushed thoroughly with nitrogen. A solution of bromine (5.79 gm, 0.0362 mol) in glacial acetic acid (10 ml) was added to the above stirred suspension at 105° C. over a period of 15 min. The reaction mixture was cooled and stirred at room temperature for 45 min. The reaction mixture was poured into aqueous 2% sodium bisulfite (200 ml) and stirred for 10 min. The precipitate was filtered washed with water (100 ml), and dried to obtain 3.5 gm of 2-bromoisovanillin as white powder mp: (200-202° C.).

Workup

  1. customThe system was flushed thoroughly with nitrogen
  2. temperatureThe reaction mixture was cooled
  3. stirringstirred for 10 min
  4. filtrationThe precipitate was filtered
  5. washwashed with water (100 ml)
  6. customdried

Sources & evidence

ORD record
ord-fd2ddee5d7df4d089a9ec83f50255d85
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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