Trifluoroiodomethane → HCID 21525915, compound

HRID 1659073Notes

Reaction equation

HRID 1659073 reaction equation
[OH:1][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:12](Br)[CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:23][C:24](I)([F:26])[F:25]>[Cu].CN(C)C=O>[OH:1][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:12]([C:24]([F:26])([F:25])[F:23])[CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 2

HCID 16843TrifluoroiodomethaneHCID 21526179HCID 21526179, compound

Product 1

HCID 21525915HCID 21525915, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 0.01 moles of ethyl α- hydroxy-γ-(3-bromo-4-cyclohexylphenyl)butyrate in 50 ml. of dimethylformamide is added 0.15 moles of trifluoromethyl iodide and 0.02 g. of copper powder. The reaction is shaken in a sealed tube for 5 hours at 140°C, cooled and then filtered and evaporated in vacuo. 200 ml. of water is added to the residue and extracted with ether. The ether extract is dried, evaporated to dryness and distilled to obtain ethyl α-hydroxy-γ-(3-trifluoromethyl-4-cyclohexylphenyl)butyrate.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. additionof water is added to the residue
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. customis dried
  8. customevaporated to dryness
  9. distillationdistilled

Sources & evidence

ORD record
ord-2906dc847bf34f44b21054915d30c9fb
Source dataset
uspto-grants-1976_06
Patent number
US03966801

Reaction notes

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