4-Iodotoluene → 4-Iodobenzyl bromide

HRID 343352Notes

Reaction equation

HRID 343352 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 122074-IodotolueneHCID 67184N-bromobutanimide

Product 1

HCID 9542584-Iodobenzyl bromideYield 45%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-iodotoluene (21.8 g, 100 mmol), N-bromosuccinimide (18.69 g, 105 mmol) and αα-azobisisobutyronitrile (100 mg) in carbon tetrachloride (100 ml) was refluxed for 20 hours. The reaction was cooled, the precipitate filtered, washed with carbon tetrachloride (50 ml), and the filtrate evaporated. The residue was chromatographed on silica, eluting with petrol (60°-80° C.) to give the product as a white solid (13 g, 45%); δH (CDCl3) 4.42 (2H, ArCH2Br), 7.11 (2H, d, J 15.3 Hz, 2-H, 6-H), 7.67 (2H, d, J 15.3 Hz, 3'-H, 5'-H).

Workup

  1. temperaturewas refluxed for 20 hours
  2. temperatureThe reaction was cooled
  3. filtrationthe precipitate filtered
  4. washwashed with carbon tetrachloride (50 ml)
  5. customthe filtrate evaporated
  6. customThe residue was chromatographed on silica
  7. washeluting with petrol (60°-80° C.)

Sources & evidence

ORD record
ord-25cc913c520f41a2ad9550a2bc70a292
Source dataset
uspto-grants-1999_01
Patent number
US05861407

Reaction notes

Loading…