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

HRID 1643366Notes

Reaction equation

HRID 1643366 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) 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-54a2b6771e514d84afe5008bb341d1f5
Source dataset
uspto-grants-2012_02
Patent number
US08119631B2

Reaction notes

Loading…