Phenethyl bromide → HCID 15342544, compound

HRID 1720060Notes

Reaction equation

HRID 1720060 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C([O-])([O-])=O.[K+].[K+].Br[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(=O)CC.C(Cl)Cl>[C:20]1([CH2:19][CH2:18][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 160545-Hydroxyindole

Product 1

HCID 15342544HCID 15342544, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A stirred mixture of 5-hydroxyindole (0.5 g, 3.8 mmol), anhydrous K2CO3 (1.58 g, 11.4 mmol), (2-bromoethyl) benzene (2.11 g, 11.4 mmol), and a catalytic amount of KI in 2-butanone (40 ml) was heated at reflux overnight under nitrogen. Once cooled to room temperature, the reaction mixture was filtered and the flitrate concentrated under reduced pressure to give an oil. The oil was taken up in CH2Cl2 (50 ml) and washed successively with 2N-NaOH (1×20 ml) and water (1×20 ml). The organic portion was dried (MgSO4) and the solvent was removed under reduced pressure to give an oil. The oil was purified by column chromatography using a solvent system of CH2Cl2 /Hexane (40:60) to give 0.42 g (47%) of 5-(2-phenylethyloxy)indole as an oil.

Workup

  1. temperatureat reflux overnight under nitrogen
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe flitrate concentrated under reduced pressure
  4. customto give an oil
  5. washwashed successively with 2N-NaOH (1×20 ml) and water (1×20 ml)
  6. dry with materialThe organic portion was dried (MgSO4)
  7. customthe solvent was removed under reduced pressure
  8. customto give an oil
  9. customThe oil was purified by column chromatography

Sources & evidence

ORD record
ord-785fcf3764f1490db455d3b98bb1bfc6
Source dataset
uspto-grants-1996_04
Patent number
US05504101

Reaction notes

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