2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-bromo-6-nitro-1H-indole

HRID 2404689Notes

Reaction equation

HRID 2404689 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[NH:7][CH2:6][CH2:5]2.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[NH:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 827562HCID 827562, compound

Product 1

HCID 197443315-bromo-6-nitro-1H-indoleYield 38%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-6-nitro-2,3-dihydro-1H-indole (20 g, 82.3 mmol) in 1,4-dioxane (400 mL) was added DDQ (30 g, 0.13 mol). The mixture was stirred at 80° C. for 2 h. The solid was filtered off and the filtrate was concentrated to dryness. The residue was purified by column chromatography on silica gel to afford 5-bromo-6-nitro-1H-indole (7.5 g, 38%).

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0ae1d197f8d24c858ba2ace1d9139dca
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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