HCID 59809570, compound → HCID 59809537, compound

HRID 2114501Notes

Reaction equation

HRID 2114501 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Br:18])[CH:3]=1>C(O)(=O)C.CO.[Zn]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Br:18])[CH:3]=1

Participants

5

Reactant 1

HCID 59809570HCID 59809570, compound2×

Product 1

HCID 59809537HCID 59809537, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 4-bromo-2-(2-bromophenylsulfanyl)-nitrobenzene, 1e (15.56 g; 40 mmol) in acetic acid (200 mL) and methanol (400 mL) was added zinc (15.7 g; 240 mmol) over a 30 min period. The mixture was heated to 40° C. for 1 h overnight, filtered, evaporated, and dried under vacuum overnight. The residue was suspended in 1N NaOH solution and extracted with methylene chloride. The organic phase was dried over MgSO4, filtered, and evaporated. The residue was purified via flash column chromatography (eluent gradient: 0 to 10% EtOAc in heptane) to yield 14.2 g (99%) of title compound 4-bromo-2-(2-bromophenylsulfanyl)-aniline, 2e.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customdried under vacuum overnight
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified via flash column chromatography (eluent gradient: 0 to 10% EtOAc in heptane)

Sources & evidence

ORD record
ord-1aeb62a6e76149deb8658341949ce2f1
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

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