2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 7-bromo-5-nitro-1H-indole

HRID 1637328Notes

Reaction equation

HRID 1637328 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 3234907-Bromo-5-nitroindoline

Product 1

HCID 38603267-bromo-5-nitro-1H-indoleYield 91.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 7-bromo-5-nitroindoline (3.0 g, 12.3 mmol) in 200 mL of acetone was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone until color of the solution turns to dark green. The reaction mixture was concentrated in vacuo and subjected to column chromatography (CHCl3, neat) to yield 2.7 g (11.2 mmol, 91%) of the indole.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d5501d51b60c44649d68070baf79e041
Source dataset
uspto-grants-2000_03
Patent number
US06040451

Reaction notes

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