Sodium Iodide → 2-(2-Iodoethoxy)naphthalene

HRID 1058749Notes

Reaction equation

HRID 1058749 reaction equation
BrC1C=CC(S(O[CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)(=O)=O)=CC=1.[I-:25].[Na+]>CC(C)=O>[I:25][CH2:12][CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 186691322-(2-Naphthyloxy)ethyl 4-Bromobenzenesulfonate

Product 1

HCID 186691652-(2-Iodoethoxy)naphthaleneYield 72.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 2-(2-naphthyloxy)ethyl 4-bromobenzenesulfonate (Preparation 10, 380 mg, 0.93 mmol) in acetone (5 mL) at room temperature was added sodium iodide (1.0 g, 6.66 mmol). The mixture was heated at 35° C. for 16 hours and then cooled. The residual precipitate was removed by filtration and the filtrate was concentrated in vacuo. The residue was partitioned between diethyl ether (20 mL) and water (20 mL). The two layers were separated and the organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound (200 mg, 72%) as a pale yellow oil.

Workup

  1. temperaturecooled
  2. customThe residual precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was partitioned between diethyl ether (20 mL) and water (20 mL)
  5. customThe two layers were separated
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-def6471ed8d94e25a99e0548e444ee9d
Source dataset
uspto-grants-2003_02
Patent number
US06518282B1

Reaction notes

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