Water → 1-[4-(2-Iodoethyl)phenyl]-5-phenylpentan-1-one

HRID 323810Notes

Reaction equation

HRID 323810 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:21])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1.[I-:22].[Na+].O>CC(=O)CC>[I:22][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:21])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 221784791-[4-(2-Bromoethyl)phenyl]-5-phenylpentan-1-one

Product 1

HCID 221784841-[4-(2-Iodoethyl)phenyl]-5-phenylpentan-1-oneYield 83.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 1-[4-(2-bromoethyl)phenyl]-5-phenylpentan-1-one (18.2 g) and sodium iodide (9.5 g) in 2-butanone (180 ml) was stirred at 60° C. for 3.5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and the solvent was distilled away under reduced pressure to give a brown oily substance (19.2 g). The obtained brown oily substance was purified by silica gel column chromatography (eluent; hexane: ethyl acetate=20:1) to give 1-[4-(2-iodoethyl)phenyl]-5-phenylpentan-1-one (17.2 g) as a yellow oily substance.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customto give a brown oily substance (19.2 g)
  6. customThe obtained brown oily substance was purified by silica gel column chromatography (eluent; hexane: ethyl acetate=20:1)

Sources & evidence

ORD record
ord-9dad978608ac411b83ecc2652a2cfb41
Source dataset
uspto-grants-2001_04
Patent number
US06214873B1

Reaction notes

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