Water → 2-Bromo-5-chlorobenzaldehyde

HRID 1081884Notes

Reaction equation

HRID 1081884 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH3:9].[OH2:10]>C(OC(=O)C)(=O)C.S(=O)(=O)(O)O.[O-2].[Cr+6].[O-2].[O-2]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]=[O:10]

Participants

6

Reactant 2

HCID 962WaterHCID 844762-Bromo-5-chlorotoluene

Product 1

HCID 153912792-Bromo-5-chlorobenzaldehyde

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 1118Sulfuric AcidSolventHCID 7918Acetic AnhydrideSolvent2×

Conditions

Temperature
-5 °C

Procedure

To the solution of 2-bromo-5-chlorotoluene (25 g) in acetic anhydride (100 ml) and sulfuric acid (20 ml) was added dropwise chromium(VI) oxide (36.5 g) in acetic anhydride (200 ml) for 3 hours at -15° C. The mixture was stirred for 1 hour at -5° C. and then poured into ice-cooled water, and extracted with ether. The organic layer was washed with water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was suspended in ethanol (100 ml) and 3N-HCl (200 ml) and refluxed for 1 hour. After removal of the solvent, water was added to the residue, and extracted with ether.

Workup

  1. additionpoured into ice-
  2. extractionextracted with ether
  3. washThe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removal of the solvent under reduced pressure
  6. temperature3N-HCl (200 ml) and refluxed for 1 hour
  7. customAfter removal of the solvent, water
  8. additionwas added to the residue
  9. extractionextracted with ether

Sources & evidence

ORD record
ord-3b8764e33c1a424f9f22c2a2f66c10a6
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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