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

HRID 750950Notes

Reaction equation

HRID 750950 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 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-e7b621ef41b345158b88dc39140fd07a
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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