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

HRID 1795706Notes

Reaction equation

HRID 1795706 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-8a991819f10c407183ee3e11571e4ef0
Source dataset
uspto-grants-2006_04
Patent number
USRE039072E1

Reaction notes

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