1-Bromo-2-fluoro-3-nitrobenzene → 6-Bromo-7-fluoro-1H-indole

HRID 2042328Notes

Reaction equation

HRID 2042328 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[F:11].[CH:12]([Mg]Br)=[CH2:13]>C1COCC1>[Br:1][C:2]1[C:3]([F:11])=[C:4]2[C:5]([CH:12]=[CH:13][NH:8]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 404274461-Bromo-2-fluoro-3-nitrobenzeneHCID 178418507HCID 178418507, compound

Product 1

HCID 591331976-Bromo-7-fluoro-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 1-bromo-2-fluoro-3-nitrobenzene (2.5 g, 11.3 mmol) in THF (25 mL) at −50° C. was added vinyl magnesium bromide (34 mL, 34 mmol) and the mixture was stirred at −40° C. for 1 h. The reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to yield a gum, which was purified by column chromatography over silica gel eluting with EtOAc/hexane to afford pure 6-bromo-7-fluoro-1H-indole. 1H NMR (400 MHz, CDCl3) δ=6.53-6.62 (m, 1H), 7.16-7.25 (m, 2H), 7.29 (d, J=8.34 Hz, 1H) and 8.36 (br. s., 1H); MS (ES+): m/z 214.08 [MH+].

Workup

  1. customThe reaction was quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customto yield a gum, which
  7. customwas purified by column chromatography over silica gel eluting with EtOAc/hexane

Sources & evidence

ORD record
ord-4fe94292f7a44194b2d3e9e065cfbad5
Source dataset
uspto-grants-2013_11
Patent number
US08586546B2

Reaction notes

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