N-bromobutanimide → 5-Bromo-3-ethoxy-2-hydroxybenzaldehyde

HRID 2079152Notes

Reaction equation

HRID 2079152 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]1[C:13]([OH:20])=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[O:16])[CH3:10]>C(#N)C>[Br:1][C:18]1[CH:19]=[C:12]([O:11][CH2:9][CH3:10])[C:13]([OH:20])=[C:14]([CH:17]=1)[CH:15]=[O:16]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68117O-Ethylvanillin

Product 1

HCID 7906815-Bromo-3-ethoxy-2-hydroxybenzaldehydeYield 33.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After adding 5.59 g of N-bromosuccinimide to a solution of 5.11 g of 3-ethoxy-2-hydroxybenzaldehyde in 100 ml of acetonitrile, the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated, water was added to the residue, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was recrystallized using t-butyl methyl ether-heptane to give 5-bromo-3-ethoxy-2-hydroxybenzaldehyde (2.53 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue, and extraction
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was recrystallized

Sources & evidence

ORD record
ord-bdcc4468c5554e05a928298d14b36784
Source dataset
uspto-grants-2011_04
Patent number
US07928228B2

Reaction notes

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