Water → 4-Bromo-7-Fluoro-5-Methyl-1H-Indole

HRID 2278399Notes

Reaction equation

HRID 2278399 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([F:11])=[CH:4][C:3]=1[CH3:12].[CH:13]([Mg]Br)=[CH2:14].O>C1COCC1>[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([F:11])=[C:6]2[C:7]=1[CH:13]=[CH:14][NH:8]2

Participants

5

Reactant 3

HCID 962WaterHCID 100369831-Bromo-4-fluoro-2-methyl-5-nitrobenzeneHCID 178418507HCID 178418507, compound

Product 1

HCID 897391374-Bromo-7-Fluoro-5-Methyl-1H-IndoleYield 16.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-bromo-4-fluoro-2-methyl-5-nitro-benzene (20 g, 0.086 mol) in THF (250 mL) at −78° C. was added vinylmagnesium bromide (300 ml, 0.3 mol) dropwise, then the mixture was stirred at −78° C. for 2 h. Water was added and the reaction allowed to warm slowly to rt. The mixture was extracted with EtOAc, dried over Na2SO4, and concentrated. The crude product was purified by silica gel column chromatography to afford 4-bromo-7-fluoro-5-methylindole (3.2 g, 16.4%).

Workup

  1. temperatureto warm slowly to rt
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ff3279810b9a414eb7d3e436640e4e58
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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