Bromine → 5-Bromo-3-ethoxy-2-hydroxybenzaldehyde

HRID 854920Notes

Reaction equation

HRID 854920 reaction equation
[Br:1]Br.[CH2:3]([O:5][C:6]1[C:7]([OH:14])=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10])[CH3:4]>Br.CC(O)=O>[Br:1][C:12]1[CH:13]=[C:6]([O:5][CH2:3][CH3:4])[C:7]([OH:14])=[C:8]([CH:11]=1)[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 68117O-Ethylvanillin

Product 1

HCID 7906815-Bromo-3-ethoxy-2-hydroxybenzaldehydeYield 39.9%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

Bromine (2.95 g, 15.95 mmol) was added to a stirring solution of 3-ethoxy-2-hydroxybenzaldehyde (5.30 g, 31.9 mmol), which was dissolved in 30% HBr/HOAc The solution was stirred for 1.5 hrs at r.t. The reaction was quenched with H2O and extracted with ethyl acetate. The organic layer was washed with sat. ammonium chloride and dried over anhydrous sodium sulfate. Upon filtration the filtrate was concentrated in vacuo and purified by flash chromatography (silica gel) and eluted with 5% EtOAc/hexanes to yield 1.56 g (20%) of the title compound as a colorless oil: ESHRMS m/z 242.9657 (M−H, C9H9O3Br, Calc'd 242.9662).

Workup

  1. customThe reaction was quenched with H2O
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with sat. ammonium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationUpon filtration the filtrate
  6. concentrationwas concentrated in vacuo
  7. custompurified by flash chromatography (silica gel)
  8. washeluted with 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-c5d6a0634b524c85b5102990773c6c39
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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