Sodium Iodide → 1-Chloro-2-(iodomethyl)benzene

HRID 363854Notes

Reaction equation

HRID 363854 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8]Br.[Na+].[I-:11]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][I:11]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 11905alpha-Bromo-o-chlorotoluene

Product 1

HCID 131593981-Chloro-2-(iodomethyl)benzeneYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-chlorophenylmethylbromide (4 g, 19.47 mmol) and NaI (14 g, 97.33 mmol) in acetone (40 ml) was stirred under reflux for 1 hour. The reaction mixture was cooled, filtered and concentrated in vacuo. The residue was triturated with hexane and filtered. The solution was concentrated in vacuo, and the resulting oil purified by flash chromatography (silica, hexane) to afford the title compound (4.67 g, 63%) as an oil: 1H NMR (CDCl3) δ7.34 (4H, m), 4.54 (2H, s).

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with hexane
  6. filtrationfiltered
  7. concentrationThe solution was concentrated in vacuo
  8. customthe resulting oil purified by flash chromatography (silica, hexane)

Sources & evidence

ORD record
ord-ebc847ec4f4c417780a76b267cde8b83
Source dataset
uspto-grants-1999_02
Patent number
US05874424

Reaction notes

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