4-Iodotoluene → 4-Iodobenzyl bromide

HRID 1082256Notes

Reaction equation

HRID 1082256 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 p-iodotoluene (4.36 g, 20 mmol, purchased from Tokyo Kasei) and N-bromosuccinimide (3.92 g, 22 mmol, purchased from Tokyo Kasei) in 60 ml of carbontetrachloride (purchased from Wako Junyaku Kogyo) was refluxed for 4 hours under irradiation by means of an incandescent lamp to give 2.67 g (yield: 45.0%) of 4-iodobenzyl bromide as a white crystalline.

Workup

  1. temperaturewas refluxed for 4 hours under irradiation by means of an incandescent lamp

Sources & evidence

ORD record
ord-af3e63e6d4b3465b88f179b8c50a39a7
Source dataset
uspto-grants-1996_12
Patent number
US05589506

Reaction notes

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