2-Bromo-4-nitroanisole → 4-bromo-5-methoxy-1H-indole

HRID 268785Notes

Reaction equation

HRID 268785 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[CH:13]([Mg]Br)=[CH2:14]>C1COCC1>[Br:1][C:2]1[C:3]([O:11][CH3:12])=[CH:4][CH:5]=[C:6]2[C:7]=1[CH:13]=[CH:14][NH:8]2

Participants

4

Reactant 2

HCID 788702-Bromo-4-nitroanisoleHCID 178418507HCID 178418507, compound

Product 1

HCID 220305584-bromo-5-methoxy-1H-indoleYield 3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −40° C. solution of 2-bromo-4-nitro-anisole (1.16 g, 5 mmol) in THF (10 ml) was added vinylmagnesium bromide (1M in THF, 15 ml). The reaction mixture was stirred for 30 min while allowing the temperature to rise to −20° C. The reaction was quenched by addition of a saturated solution of NH4Cl, diluted with Et2O, and the aqueous layer was extracted twice with Et2O. The combined organic layers were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) to provide 4-bromo-5-methoxyindole XLVI (38 mg, 3% yield) as an oil.

Workup

  1. customto rise to −20° C
  2. customThe reaction was quenched by addition of a saturated solution of NH4Cl
  3. additiondiluted with Et2O
  4. extractionthe aqueous layer was extracted twice with Et2O
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-f21fbc06921944cb872012656c186511
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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