(E)-1-(4-bromo-2-nitrostyryl)pyrrolidine → 4-Bromo-2-nitrobenzaldehyde

HRID 593423

Reaction equation

HRID 593423 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[Br:7][C:8]1[CH:20]=[CH:19][C:11](/[CH:12]=C/N2CCCC2)=[C:10]([N+:21]([O-:23])=[O:22])[CH:9]=1>C1COCC1.O>[Br:7][C:8]1[CH:20]=[CH:19][C:11]([CH:12]=[O:2])=[C:10]([N+:21]([O-:23])=[O:22])[CH:9]=1

Participants

4

Reactant 2

HCID 10913500(E)-1-(4-bromo-2-nitrostyryl)pyrrolidineHCID 23667635Sodium periodate

Product 1

HCID 6080994-Bromo-2-nitrobenzaldehydeYield 86%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of sodium periodate (298 g, 1.40 mol) in THF—H2O (4 L, 1:1) at 0° C. was added (E)-1-(4-bromo-2-nitrostyryl)pyrrolidine (138 g, 464 mmol). The mixture was stirred for 15 h and then filtered to remove solid precipitates. The aqueous layer from the filtrate was separated and extracted with EtOAc (4×200 mL). The combined organic layers were washed with H2O (2×200 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude product that was purified by silica gel flash column chromatography (5% EtOAc in hexanes) to afford 91 g (86%) of 4-bromo-2-nitrobenzaldehyde.

Workup

  1. filtrationfiltered
  2. customto remove solid
  3. customprecipitates
  4. customThe aqueous layer from the filtrate was separated
  5. extractionextracted with EtOAc (4×200 mL)
  6. washThe combined organic layers were washed with H2O (2×200 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give the crude product that
  11. customwas purified by silica gel flash column chromatography (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-208699a64650400482dcca443a515697
Source dataset
uspto-grants-2016_01
Patent number
US09242964B2

Linked notes

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