Sodium Iodide → Ethyl alpha-iodo-3-chloro-4-cyclohexylphenylacetate

HRID 436320Notes

Reaction equation

HRID 436320 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:10]([Cl:20])[CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[I-:21].[Na+]>CC(C)=O>[I:21][CH:2]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:10]([Cl:20])[CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 21454151Ethyl alpha-bromo-3-chloro-4-cyclohexylphenylacetate

Product 1

HCID 21454139Ethyl alpha-iodo-3-chloro-4-cyclohexylphenylacetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 40.5 g. (0.1 moles) of ethyl α-bromo-3-chloro-4-cyclohexylphenylacetate and 150 g. of sodium iodide in 1 liter of anhydrous acetone is refluxed for 4 hours. The reaction mixture is then evaporated to dryness and extracted with ether. The ether is then washed with water, dried and evaporated to dryness to obtain ethyl α-iodo-3-chloro-4-cyclohexylphenylacetate.

Workup

  1. additionA mixture of 40.5 g
  2. customThe reaction mixture is then evaporated to dryness
  3. extractionextracted with ether
  4. washThe ether is then washed with water
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-fb8e13dbca504f08ad2b7e6d63363ee4
Source dataset
uspto-grants-1977_02
Patent number
US04008269

Reaction notes

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