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

HRID 1622095Notes

Reaction equation

HRID 1622095 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:11]=[CH:12][C:13]([OH:18])=[C:14]([CH:17]=1)[CH:15]=[O:16]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:12]1[C:13]([OH:18])=[C:14]([CH:17]=[C:10]([F:9])[CH:11]=1)[CH:15]=[O:16]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27373285-Fluorosalicylaldehyde

Product 1

HCID 231489553-Bromo-5-fluoro-2-hydroxybenzaldehydeYield 77.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-bromosuccinimide (1.51 g, 8.52 mmol) was added to a magnetically stirred solution of 5-fluoro-2-hydroxybenzaldehyde (1 g, 7.1 mmol) in DMF (10 mL) and the mixture was stirred at room temperature for 5 hour. The mixture was diluted with ethyl acetate and the organic layer was washed with 5% citric acid, brine, dried over anhydrous sodium sulfate and concentrated by evaporation. Product was purified from the residue by chromatography over silica gel employing 50% ethyl acetate/hexanes to give 3-bromo-5-fluoro-2-hydroxybenzaldehyde (1.2 g).

Workup

  1. washthe organic layer was washed with 5% citric acid, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated by evaporation
  4. customProduct was purified from the residue by chromatography over silica gel employing 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9713a7db9a5f49e6a03734c7adfddfb0
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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