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

HRID 2402691Notes

Reaction equation

HRID 2402691 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-f24d9d02c4c5402784f9f45d7ed8f563
Source dataset
uspto-grants-2014_08
Patent number
US08796455B2

Reaction notes

Loading…