Sodium Hydroxide → 7-Bromo-3-chloro-4-methyl-1H-indole

HRID 1173095Notes

Reaction equation

HRID 1173095 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:19])=[C:14]2[C:18]=1[NH:17][CH:16]=[CH:15]2.BrC1C=CC(C)=CC=1[N+]([O-])=O.[OH-].[Na+]>C(#N)C>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:19])=[C:14]2[C:18]=1[NH:17][CH:16]=[C:15]2[Cl:1]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 792244-Bromo-3-nitrotolueneHCID 187528627-bromo-4-methyl-1H-indole

Product 1

HCID 223592387-Bromo-3-chloro-4-methyl-1H-indoleYield 99.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.0 g (30.0 mmol) of N-chlorosuccinimide was added to an acetonitrile solution (250 ml) containing 5.8 g (27.6 mmol) of 7-bromo-4-methyl-1H-indole synthesized from 2-bromo-5-methylnitrobenzene in the same manner as in Production Example 1a, followed by stirring at room temperature overnight. 50 ml of a 1N aqueous sodium hydroxide was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated. Then, the residue was purified by silica gel column chromatography, to give 6.7 g of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThen, the residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d235fdf7bdbd4931b5e69360ffa74e6f
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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