Ammonium Chloride → 7-Bromo-6-fluoro-1H-indole

HRID 1512837Notes

Reaction equation

HRID 1512837 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][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[C:7]([F:8])=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:9][CH:13]=[CH:12]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 183734742-Bromo-1-fluoro-3-nitrobenzeneHCID 178418507HCID 178418507, compound

Product 1

HCID 269860207-Bromo-6-fluoro-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-bromo-3-fluoro-1-nitrobenzene (13 g) in anhydrous THF (80 mL) was added 1 M vinylmagnesium bromide in THF (178 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 NH4Cl solution, the organic phase was separated by extraction with EtOAc (3×200 mL). Purification by column chromatography afforded of 7-bromo-6-fluoro-1H-indole (D140) (3 g) as a brown oil.

Workup

  1. customthe organic phase was separated by extraction with EtOAc (3×200 mL)
  2. customPurification by column chromatography

Sources & evidence

ORD record
ord-079d3fcfd9d14241978a39fd61ce185e
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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