Sodium Iodide → 1-Benzyloxy-2-iodoethane

HRID 1826475Notes

Reaction equation

HRID 1826475 reaction equation
BrC1C=CC(S(O[CH2:12][CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=O)=O)=CC=1.[I-:22].[Na+]>CC(C)=O>[I:22][CH2:12][CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 20702450(Benzyloxy)ethyl 4-bromobenzenesulfonate

Product 1

HCID 103553141-Benzyloxy-2-iodoethaneYield 88.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (benzyloxy)ethyl 4-bromobenzenesulfonate (Preparation 89, 6.92 g, 19.5 mmol) in acetone (60 ml) was added sodium iodide (5.84 g, 39.0 mmol) and the reaction mixture was left to stir at room temperature for 16 h. The resulting precipitate was filtered and the filtrate was concentrated in vacuo. The crude residue was dissolved in dichloromethane and washed with aqueous sodium thiosulphate solution and then with water (2×60 ml). The organic layer was dried (Na2SO4) and concentrated in vacuo to give the title compound as a pale brown oil (4.5 g, 88%).

Workup

  1. waitthe reaction mixture was left
  2. filtrationThe resulting precipitate was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe crude residue was dissolved in dichloromethane
  5. washwashed with aqueous sodium thiosulphate solution
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d574e6e102f340cab66628800d3f040e
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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