4-Bromo-2-nitroanisole → 4-Bromo-7-methoxy-1H-indole

HRID 1716659Notes

Reaction equation

HRID 1716659 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.[CH:13]([Mg]Br)=[CH2:14]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]2[C:3]=1[CH:13]=[CH:14][NH:10]2

Participants

4

Reactant 2

HCID 1185334-Bromo-2-nitroanisoleHCID 178418507HCID 178418507, compound

Product 1

HCID 468355404-Bromo-7-methoxy-1H-indoleYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −60° C. solution of 4-bromo-2-nitroanisole (7.89 g, 33.3 mmol) in THF (300 was added vinylmagnesium bromide (1 M in THF, 100 ml, 0.1 mol) while maintaining the reaction temperature below −40° C. The resulting mixture was stirred allowing the temperature to rise to −40° C. in 2 hours. The reaction mixture was then quenched with a saturated solution of NH4Cl (700 ml) and extracted with Et2O (200 ml). The combined organic layers were washed with brine, dried over MgSO4, filtered, concentrated, and purified through flash chromatography affording 4-bromo-7-methoxyindole LII (594 mg, 8% yield).

Workup

  1. temperaturewhile maintaining the reaction temperature below −40° C
  2. customThe reaction mixture was then quenched with a saturated solution of NH4Cl (700 ml)
  3. extractionextracted with Et2O (200 ml)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified through flash chromatography

Sources & evidence

ORD record
ord-43cf058aca7748dfb87cad6dacbcd266
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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