Water → 4-Bromo-5,7-dimethyl-1H-indole

HRID 2278397Notes

Reaction equation

HRID 2278397 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([CH3:11])=[CH:4][C:3]=1[CH3:12].[CH:13]([Mg]Br)=[CH2:14].O>C1COCC1>[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([CH3:11])=[C:6]2[C:7]=1[CH:13]=[CH:14][NH:8]2

Participants

5

Reactant 3

HCID 962WaterHCID 124743261-Bromo-2,4-dimethyl-5-nitrobenzeneHCID 178418507HCID 178418507, compound

Product 1

HCID 533995074-Bromo-5,7-dimethyl-1H-indoleYield 31.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 1-bromo-2,4-dimethyl-5-nitro-benzene (7.5 g, 32.6 mmol) in THF (100 mL) at −78° C. was added vinylmagnesium bromide (110 mL of 1.0 M solution in THF, 1.1 mol) dropwise. The reaction was allowed to warm slowly to −40° C. then stirred for 4 h. Water was added, and the reaction mixture allowed to warm slowly to rt and extracted with EtOAc. The organic phase was then dried over Na2SO4 and concentrated to give 4-bromo-5,7-dimethylindole (2.3 g) which was used in the subsequent step without purification.

Workup

  1. temperatureto warm slowly to rt
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was then dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fe90991f25d94f1b84f42f8b971910a3
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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