Ethyl Acetate → 7-bromo-4-methyl-1H-indole

HRID 1838048Notes

Reaction equation

HRID 1838048 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-])=O.[CH:12]([Mg]Br)=[CH2:13].[Cl-].[NH4+].C(OCC)(=O)C>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]2[C:3]=1[NH:9][CH:13]=[CH:12]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 792244-Bromo-3-nitrotolueneHCID 178418507HCID 178418507, compound

Product 1

HCID 187528627-bromo-4-methyl-1H-indoleYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 300 ml of a solution of 65.0 g (301 mmol) of 2-bromo-5-methylnitrobenzene in tetrahydrofuran was added 1 liter of a 1.0M solution of vinyl magnesium bromide (1 mol) in tetrahydrofuran at −60° C. in a nitrogen atmosphere under stirring during 1 hour. To the reaction mixed solution were added a saturated aqueous solution of ammonium chloride and ethyl acetate, and the resulting insoluble matters were filtered off. The resulting filtrate was dried over magnesium sulfate, concentrated, and then the resulting residue was purified by a silica gel column chromatography to give 35.5 g of the title compound.

Workup

  1. additionTo the reaction mixed solution
  2. filtrationthe resulting insoluble matters were filtered off
  3. dry with materialThe resulting filtrate was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customthe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-7ff384c538e44dc0b7095cdcdb271b1f
Source dataset
uspto-grants-2004_01
Patent number
US06673787B2

Reaction notes

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