4-Chlorobenzyl cyanide → HCID 69976413, compound

HRID 1168416Notes

Reaction equation

HRID 1168416 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[F:11][C:12]([F:25])([F:24])[C:13]1[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=1[C:15](OCC)=[O:16].CC[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[C:15]([OH:16])[C:14]2[CH:20]=[CH:21][CH:22]=[CH:23][C:13]=2[C:12]([F:11])([F:24])[F:25])[C:7]#[N:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2415824-Chlorobenzyl cyanideHCID 521815Ethyl 2-(trifluoromethyl)benzoateHCID 2723922Sodium ethoxide

Product 1

HCID 69976413HCID 69976413, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.8 g of 4-chlorobenzyl cyanide, 10 g of ethyl 2-trifluoromethylbenzoate and 2.9 g of sodium ethylate were added to 100 ml of toluene and then reacted for 8 hours under reflux. The reaction mixture was returned to room temperature and extracted by an addition of 200 ml of water. The aqueous phase was adjusted to pH 6 to 7 with 6N hydrochloric acid and then extracted by an addition of 400 ml of methylene chloride. The organic layer was washed with water and a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 6.3 g of the desired product. The NMR spectrum data of this product were the same as in Reference Preparation Example 3.

Workup

  1. customreacted for 8 hours
  2. temperatureunder reflux
  3. customwas returned to room temperature
  4. extractionextracted by an addition of 200 ml of water
  5. extractionextracted by an addition of 400 ml of methylene chloride
  6. washThe organic layer was washed with water
  7. dry with materiala saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a8c7a45f5c16410eb7a494ff35233fb2
Source dataset
uspto-grants-2003_09
Patent number
US06624179B1

Reaction notes

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