Ethyl Bromide → 4-Ethoxy-1H-indole

HRID 1830019Notes

Reaction equation

HRID 1830019 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH2:11](Br)[CH3:12].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH2:11]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)[CH3:12]

Participants

4

Reactant 3

HCID 6332Ethyl BromideHCID 10796Cesium carbonateHCID 754211H-indol-4-ol

Product 1

HCID 153707174-Ethoxy-1H-indole

Procedure

4-Hydroxyindole (1.0 equivalents) is dissolved in dry, degassed acetone. EtBr (5.0 equivalents) and Cs2CO3 (2.5 equivalents) are added, and the resulting solution is stirred for 18 hours. The reaction mixture is filtered through a Celite plug. The solvent is evaporated, and the product is purified by flash chromatography (MeOH:CH2Cl2, 5:95) to yield the title compound.

Workup

  1. customin dry
  2. customdegassed acetone
  3. filtrationThe reaction mixture is filtered through a Celite plug
  4. customThe solvent is evaporated
  5. customthe product is purified by flash chromatography (MeOH:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-50ad1b6749b74c6a9e56a02eae1e3b3d
Source dataset
uspto-grants-2006_06
Patent number
US07064215B2

Reaction notes

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