Water → 2-(4-Bromophenyl)-1-methyl-1H-indole

HRID 861413Notes

Reaction equation

HRID 861413 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][CH:9]=1.IC.O>CN(C)C=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:15]([CH3:1])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 6232522-(4-Bromophenyl)-1H-indoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 123487182-(4-Bromophenyl)-1-methyl-1H-indoleYield 56.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium tert-butoxide (1.23 g) was added to a solution of 2-(4-bromophenyl)indole (2.72 g) in dimethylformamide (40 ml). Iodomethane (1.25 ml) was added and the reaction mixture stirred at ambient temperature for 18 hours. The reaction mixture was added to water. This solid was collected by filtration and purified by vacuum chromatography on silica gel (Merck Art. 7736) using 5% ethyl acetate/hexane as eluent to give 2-(4-bromophenyl)-1-methylindole (1.625 g) as a solid, m.p. 114°-115° C.

Workup

  1. filtrationThis solid was collected by filtration
  2. custompurified by vacuum chromatography on silica gel (Merck Art. 7736)

Sources & evidence

ORD record
ord-833344d2b71247ba9c9975f6a28fa74b
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

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