4-Bromo-7-nitrobenzofurazan → HCID 21875029, compound

HRID 723671Notes

Reaction equation

HRID 723671 reaction equation
[Br:1][C:2]1[C:7]2=[N:8][O:9][N:10]=[C:6]2[C:5]([N+:11]([O-])=O)=[CH:4][CH:3]=1>CC(O)=O>[Br:1][C:2]1[C:7]2=[N:8][O:9][N:10]=[C:6]2[C:5]([NH2:11])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 120102144-Bromo-7-nitrobenzofurazan

Product 1

HCID 21875029HCID 21875029, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of compound 422A (563 mg, 2.31 mmol) in AcOH (5 mL) was heated to 70° C. and Fe0 powder (258 mg, 4.62 mmol) was added in one portion. The resulting dark reaction mixture was stirred for 15 min, cooled to rt and concentrated under reduced pressure. The residue was taken up in EtOAc and the resulting solution was washed with sat. Na2CO3 solution. The organic layer was dried over Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel eluting with 10–60% EtOAc in hexanes to give 470 mg (95%) of compound 422B as a red solid.

Workup

  1. customThe resulting dark reaction mixture
  2. concentrationconcentrated under reduced pressure
  3. washthe resulting solution was washed with sat. Na2CO3 solution
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography on silica gel eluting with 10–60% EtOAc in hexanes

Sources & evidence

ORD record
ord-fbaaa7c329494defb29c6b7703627a83
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

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