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

HRID 426801Notes

Reaction equation

HRID 426801 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-fb495f4f07db4aa89914ee68a9c3d722
Source dataset
uspto-grants-1979_10
Patent number
US04171373

Reaction notes

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