Sodium Iodide → (2-Iodoethyl)cyclohexane

HRID 2103586Notes

Reaction equation

HRID 2103586 reaction equation
Br[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[I-:10].[Na+]>CC(C)=O>[I:10][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 15440(2-Bromoethyl)cyclohexane

Product 1

HCID 12923931(2-Iodoethyl)cyclohexaneYield 85.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolve (2-bromo-ethyl)-cyclohexane (10.0 g, 52.3 mmol) in 500 mL acetone, add sodium iodide (15.6 g, 104.6 mmol) and reflux over night. Filter the reaction mixture, add water to the filtrate and extract with hexane. Dry the organic phases over sodium sulfate, filter and concentrate to an oil. Further purify this material by distillation to afford the title compound (10.6 g). 1H-NMR (CDCl3) δ=0.83-1.00 (m, 2H), 1.07-1.48 (m, 4H), 1.61-1.80 (m, 7H), 3.16-3.27 (m, 2H).

Workup

  1. temperaturereflux over night
  2. filtrationFilter the reaction mixture
  3. additionadd water to the filtrate
  4. extractionextract with hexane
  5. dry with materialDry the organic phases over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate to an oil
  8. customFurther purify this material
  9. distillationby distillation

Sources & evidence

ORD record
ord-e9766b19f5fb475ea8c723f0880d395b
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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