Sodium Iodide → 1-(4-Iodobutyl)-4-methoxybenzene

HRID 1768048Notes

Reaction equation

HRID 1768048 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.[I-:14].[Na+]>CC(C)=O>[I:14][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 5781911-(4-Bromobutyl)-4-methoxybenzene

Product 1

HCID 2848841-(4-Iodobutyl)-4-methoxybenzeneYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture consisting of 30.2 g (124 mmol) 1-(4-bromo-butyl)-4-methoxy-benzene, 19.2 g (128 mmol) sodium iodide and 508 ml acetone was heated to reflux temperature for 1 h. The resulting suspension was cooled to r.t. and the precipitated sodium bromide removed by filtration. The filtrate was stripped off the solvents by vacuum distillation and the residue distributed between water and diethyl ether. After drying of the organic phase over sodium sulphate, vacuum distillation gave 34.9 g (97%) of the title compound as slightly yellow coloured liquid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature for 1 h
  3. customthe precipitated sodium bromide removed by filtration
  4. distillationby vacuum distillation
  5. dry with materialAfter drying of the organic phase over sodium sulphate, vacuum distillation

Sources & evidence

ORD record
ord-ecf8dad1d67945f08e39f0af42ad39ee
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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