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

HRID 2230433Notes

Reaction equation

HRID 2230433 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 cnromatography (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 cnromatography (silica, hexane)

Sources & evidence

ORD record
ord-8611708aa96f4a53968a7aadb6ce514b
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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