Trifluoroiodomethane → Ethyl 3-chloro-5-trifluoromethyl-4-cyclohexylphenylglyoxylate

HRID 839653Notes

Reaction equation

HRID 839653 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:15](=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[C:6]([Cl:14])[C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[F:22][C:23](I)([F:25])[F:24]>[Cu].CN(C)C=O>[Cl:14][C:6]1[CH:5]=[C:4]([C:15](=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:3]=[C:2]([C:23]([F:25])([F:24])[F:22])[C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 16843TrifluoroiodomethaneHCID 20515177Ethyl 3-bromo-5-chloro-4-cyclohexylphenylglyoxylate

Product 1

HCID 20515171Ethyl 3-chloro-5-trifluoromethyl-4-cyclohexylphenylglyoxylate

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 0.01 moles of ethyl 3-bromo-5-chloro-4-cyclohexylphenylglyoxylate 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, 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 3-chloro-5-trifluoromethyl-4-cyclohexylphenylglyoxylate.

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-b78cd8de343f41c7b5080c72ae9dd785
Source dataset
uspto-grants-1978_06
Patent number
US04096279

Reaction notes

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