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

HRID 1698674Notes

Reaction equation

HRID 1698674 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-d78422caa71d40a7b996701b4e26aa59
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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