Trifluoroiodomethane → Ethyl 3-trifluoromethyl-4-cyclohexylphenylglyoxylate

HRID 616735

Reaction equation

HRID 616735 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[F:21][C:22](I)([F:24])[F:23]>[Cu].CN(C)C=O>[F:21][C:22]([F:24])([F:23])[C:2]1[CH:3]=[C:4]([C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 16843TrifluoroiodomethaneHCID 20515211Ethyl 3-bromo-4-cyclohexylphenylglyoxylate

Product 1

HCID 20515217Ethyl 3-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-4-cyclohexylphenyl-glyoxylate in 50 ml. of dimethylformamide is added 0.15 moles of trifluoro-methyl 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 3-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-96c33b18f2994a9cbd36a9eb5a0fdda3
Source dataset
uspto-grants-1978_02
Patent number
US04075354

Linked notes

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