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2,3-Dichloronitrobenzene → 6,7-dichloro-1H-indole

HRID 18503
Notes
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Reaction equation

HRID 18503 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:7]=1[N+:13]([O-])=O.[NH4+].[Cl-]>C1COCC1>[Cl:12][C:11]1[C:6]([Cl:5])=[C:7]2[C:8]([CH:1]=[CH:2][NH:13]2)=[CH:9][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 185552,3-DichloronitrobenzeneHCID 25517Ammonium ChlorideHCID 178418507HCID 178418507, compound

Product 1

HCID 122728026,7-dichloro-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

800 ml of a 1M solution of vinylmagnesium bromide in THF are cooled to −45° C. under a nitrogen atmosphere, a solution of 51.2 g of 2,3-dichloronitrobenzene in 1000 ml of THF is then added dropwise and the mixture is left stirring at −30° C. for 1 hour. The reaction mixture is poured onto 1000 ml of a saturated NH4Cl solution and extracted with ether, the combined organic phases are washed with water and with a saturated NaCl solution and dried over MgSO4, and the solvents are evaporated under vacuum. The residue is chromatographed on silica gel, elution being carried out with a cyclohexane/EtOAc mixture (95/5; v/v). 27.75 g of the expected compound are obtained.

Workup

  1. waitthe mixture is left
  2. extractionextracted with ether
  3. washthe combined organic phases are washed with water and with a saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. customthe solvents are evaporated under vacuum
  6. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-20708af8b784463d960ef216aa77f69e
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07741363B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes