4-Bromo-2-nitrotoluene → 4-Bromo-7-methyl-1H-indole

HRID 2365188Notes

Reaction equation

HRID 2365188 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.[CH:12]([Mg]Br)=[CH2:13]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]2[C:3]=1[CH:12]=[CH:13][NH:9]2

Participants

4

Reactant 2

HCID 1235464-Bromo-2-nitrotolueneHCID 178418507HCID 178418507, compound

Product 1

HCID 247292794-Bromo-7-methyl-1H-indoleYield 35.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 4-bromo-2-nitrotoluene (3.0 g, 13.9 mmol) in THF (40 mL) at −40° C. was added vinyl magnesium bromide (48.6 mmol, 48.6 mL; 1.0 M in THF) dropwise over 15 minutes and the mixture stirred at −40° C. for 1.5 hours. The reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organic layers were washed with brine, separated and dried (MgSO4). The residue was evaporated and purified by column chromatography to yield 4-bromo-7-methylindole (1.03 g).

Workup

  1. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. customseparated
  5. dry with materialdried (MgSO4)
  6. customThe residue was evaporated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-40663b4b65fb442b8279d9ff21ef5a6d
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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