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

HRID 1532889Notes

Reaction equation

HRID 1532889 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 (4.67g, 63%) as an oil: 1H NMR (CDCl3) δ 7.34 (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-6c27340b15f246719bec10a3a9e35dd6
Source dataset
uspto-grants-2001_03
Patent number
US06204261B1

Reaction notes

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