Tetrahydrofuran → 4-Bromo-2-nitrobenzaldehyde

HRID 1873502Notes

Reaction equation

HRID 1873502 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=C/N(C)C)=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1.C1C[O:19]CC1>P([O-])([O-])([O-])=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:19])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 11207982HCID 11207982, compound

Product 1

HCID 6080994-Bromo-2-nitrobenzaldehydeYield 28%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

To a solution of crude (E)-2-(4-bromo-2-nitrophenyl)-N,N-dimethylethenamine (35.5 g, 131 mmol) in THF (300 mL) and pH 7.2 phosphate buffer (300 mL) was added NaIO4 (56.0 g, 262 mmol). The solids were removed and the filter cake was washed with EtOAc (200 mL). The filtrate was washed with brine (2×100 mL), dried and concentrated. The concentrate was purified via flash chromatography (5% EtOAc/hexanes to 10% EtOAc/hexanes) to provide 4-bromo-2-nitrobenzaldehyde (8.41 g, 28% yield).

Workup

  1. customThe solids were removed
  2. washthe filter cake was washed with EtOAc (200 mL)
  3. washThe filtrate was washed with brine (2×100 mL)
  4. customdried
  5. concentrationconcentrated
  6. customThe concentrate was purified via flash chromatography (5% EtOAc/hexanes to 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ba9554b68f2a456ca09b73490e47f11d
Source dataset
uspto-grants-2012_11
Patent number
US08304407B2

Reaction notes

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