Ammonium Chloride → 7-bromo-5-fluoro-1H-indole

HRID 1512829Notes

Reaction equation

HRID 1512829 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-])=O.[CH:12]([Mg]Br)=[CH2:13].[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]2[C:3]=1[NH:9][CH:13]=[CH:12]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 27569932-Bromo-4-fluoro-1-nitrobenzeneHCID 178418507HCID 178418507, compound

Product 1

HCID 38528797-bromo-5-fluoro-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-bromo-4-fluoro-1-nitrobenzene (24 g) in anhydrous THF (200 mL) was added 1 M vinylmagnesium bromide in THF (328 mL) dropwise at −78° C. slowly, then the mixture was allowed to warm to RT and stirred for 2 hours. TLC indicated the reaction was complete. The reaction mixture was poured into saturated aqueous NH4Cl solution. The organic phase was separated by extraction with EA (3×200 mL). The crude product was purified by column chromatography to afford 7-bromo-5-fluoro-1H-indole (D131) (15 g) as a brown oil.

Workup

  1. customThe organic phase was separated by extraction with EA (3×200 mL)
  2. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-b3728f84b364462292e397989262e692
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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