4-Bromo-2-nitrobenzene-1-thiol → 2-amino-4-bromobenzene-1-thiol

HRID 900188Notes

Reaction equation

HRID 900188 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.[H][H]>C1COCC1.[Ni]>[NH2:9][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[SH:8]

Participants

5

Reactant 2

HCID 219800194-Bromo-2-nitrobenzene-1-thiol2×HCID 178418361HCID 178418361, compound

Product 1

HCID 121992942-amino-4-bromobenzene-1-thiol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 4-bromo-2-nitro-benzenethiol and its disulfide from Example 2A (14.9 g, 53.5 mmol) in THF (450 mL) was mixed with Raney Ni (30 g, 100% wt). The mixture was hydrogenated in a 1000 mL Paar shaker at a hydrogen pressure of 40 psi at 50° C. for 41 hours. When the reaction was complete, the solids were filtered. The solid filter-cake was dissolved in pyridine (600 mL) at 100° C. and filtered to remove the Ni residue. This pyridine solution contained mostly the 2-amino-4-bromophenyldisulfide. Crude yield=11.9 g (92%)

Workup

  1. filtrationthe solids were filtered
  2. filtrationThe solid filter-cake
  3. dissolutionwas dissolved in pyridine (600 mL) at 100° C.
  4. filtrationfiltered
  5. customto remove the Ni residue

Sources & evidence

ORD record
ord-b0d9410dcbfa42b19d62928123fbc69f
Source dataset
uspto-grants-2008_04
Patent number
US07358263B2

Reaction notes

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