Tetrahydrofuran → 7-bromo-4-methyl-1H-indole

HRID 1173087

Reaction equation

HRID 1173087 reaction equation
O1CCCC1.[CH:6]([Mg]Br)=[CH2:7].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[N+:18]([O-])=O.[Cl-].[NH4+]>C(OCC)(=O)C>[Br:10][C:11]1[CH:16]=[CH:15][C:6]([CH3:7])=[C:13]2[C:12]=1[NH:18][CH:17]=[CH:14]2

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 792244-Bromo-3-nitrotolueneHCID 178418507HCID 178418507, compound

Product 1

HCID 187528627-bromo-4-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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

Workup

  1. filtrationthe insoluble matters were filtered off
  2. dry with materialThe filtrate was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThen, the residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dfbab5c697244738928f3dd8cc579791
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Linked notes

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