4-Bromo-2-nitrobenzaldehyde → 2-Amino-4-bromobenzaldehyde

HRID 2079639Notes

Reaction equation

HRID 2079639 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-])=O)[CH:3]=1>C(O)(=O)C.C(O)C.[Fe]>[NH2:10][C:4]1[CH:3]=[C:2]([Br:1])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

5

Reactant 1

HCID 6080994-Bromo-2-nitrobenzaldehyde

Product 1

HCID 179145982-Amino-4-bromobenzaldehydeYield 38%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a 0.2M solution of 4-bromo-2-nitrobenzaldehyde in acetic acid and ethanol (v/v 1:1) solvent system was added iron powder. The reaction mixture was stirred at ambient temperature under Argon for 1.5 h and LCMS showed the reaction was complete. Insoluble solid was filtered off and the filtrate was concentrated in vacuum. Residue was diluted with ethyl acetate and was washed with saturated sodium bicarbonate, brine, dried over sodium sulfate and concentrated. Crude product was purified by Biotage using 15% ethyl acetate in hexane to give desired product in 38% yield. ES/MS m/z 200/202 (MH+).

Workup

  1. filtrationInsoluble solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuum
  3. additionResidue was diluted with ethyl acetate
  4. washwas washed with saturated sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customCrude product was purified by Biotage

Sources & evidence

ORD record
ord-ecedf01c9a974c0580f53f6ef7948999
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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