Water → HCID 53844947, compound

HRID 894579Notes

Reaction equation

HRID 894579 reaction equation
[Cl:1][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:3][CH:4]1[CH:6]([C:7](Cl)=[O:8])[C:5]1([CH3:11])[CH3:10].[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][C:20]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C-:34]#[N:35].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.CCCCCC>[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]([O:24][C:7]([CH:6]2[CH:4]([CH:3]=[C:2]([Cl:1])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]2([CH3:11])[CH3:10])=[O:8])[C:34]#[N:35])=[CH:21][C:20]=1[O:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 1100684-Fluoro-3-phenoxybenzaldehydeHCID 54515456HCID 54515456, compound

Product 1

HCID 53844947HCID 53844947, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

8.1 g (0.03 mole) of 3-(2-chloro-2-phenyl-vinyl)-2,2-dimethyl-cyclopropane-carboxylic acid chloride and 6.5 g (0.03 mole) of 4-fluoro-3-phenoxy-benzaldehyde are added dropwise to a mixture of 2.25 g of sodium cyanide, 3.5 ml of water, 150 ml of n-hexane and 0.75 g of tetrabutylammonium bromide at 20° to 25° C., whilst stirring. The reaction mixture is then stirred at 20° to 25° C. for 4 hours and is subsequently diluted with 300 ml of toluene and washed twice with 300 ml of water each time. The organic phase is dried over magnesium sulphate and the solvent is distilled off under a waterpump vacuum. Last residues of solvent are removed by brief incipient distillation at 60° C./1 mbar. 10.8 g (76% of theory) of 3-(2-chloro-2-phenyl-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid 4-fluoro-3-phenoxy-α-cyano-benzyl ester are obtained as a viscous oil.

Workup

  1. stirringThe reaction mixture is then stirred at 20° to 25° C. for 4 hours
  2. washwashed twice with 300 ml of water each time
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. distillationthe solvent is distilled off under a waterpump vacuum
  5. customLast residues of solvent are removed by brief incipient distillation at 60° C./1 mbar

Sources & evidence

ORD record
ord-00e295bd004548a296bb368e02d04843
Source dataset
uspto-grants-1981_08
Patent number
US04284645

Reaction notes

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