5-Bromo-4-methoxybenzofurazanoxide → 4-Bromo-3-methoxyphenylene-1,2-diamine

HRID 475090Notes

Reaction equation

HRID 475090 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([C:11]=1[O:12][CH3:13])=[N:7]O[N+:9]=2[O-]>CCOC(C)=O.[Pd]>[Br:1][C:2]1[C:11]([O:12][CH3:13])=[C:6]([NH2:7])[C:5]([NH2:9])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 712718545-Bromo-4-methoxybenzofurazanoxide

Product 1

HCID 670624754-Bromo-3-methoxyphenylene-1,2-diamineYield 63.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 2 L Parr shaker bottle was dried and cooled under a stream of nitrogen then charged with 5-bromo-4-methoxybenzofurazanoxide (100 g, 0.44 mol, 1.0 equiv.) in EtOAc (1 L) and 10% Pd/C (10% w/w, 10.0 g) was added. The reaction was then stirred at RT overnight under hydrogen. The reaction mixture was filtered through a Celite® pad and concentrated in vacuo to afford 4-bromo-3-methoxy-benzene-1,2-diamine (61.0 g, crude) as a dark brown semi solid. The crude material was taken directly to the next step.

Workup

  1. customA 2 L Parr shaker bottle was dried
  2. temperaturecooled under a stream of nitrogen
  3. additionwas added
  4. filtrationThe reaction mixture was filtered through a Celite® pad
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e99735c1f99452da16dd273120cbe9b
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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