Water → HCID 86738077, compound

HRID 622723Notes

Reaction equation

HRID 622723 reaction equation
[Cl:1]/[C:2](/[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:3]\[C@H:4]1[C@H:6]([C:7](Cl)=[O:8])[C:5]1([CH3:11])[CH3:10].[C-:19]#[N:20].[Na+].O.[O:23]([C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1[F:38])[CH:33]=[O:34])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1CCCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:19]([CH:33]([O:34][C:7]([C@H:6]1[C@H:4](/[CH:3]=[C:2](\[Cl:1])/[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:5]1([CH3:11])[CH3:10])=[O:8])[C:32]1[CH:35]=[CH:36][C:37]([F:38])=[C:30]([O:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:31]=1)#[N:20]

Participants

8

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 1100684-Fluoro-3-phenoxybenzaldehydeHCID 44152741rel-(1R,3R)-3-[(1Z)-2-Chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarbonyl chloride

Product 1

HCID 86738077HCID 86738077, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8078CyclohexaneSolvent2×

Procedure

3.4 g (0.0112 mole) of (+)-trans-Z-3-(2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid chloride, dissolved in 10 ml of cyclohexane, were added dropwise to a mixture of 50 ml of cyclohexane, 0.87 g of sodium cyanide, 1.3 ml of water, 2.42 g (0.0112 mole) of 3-phenoxy-4-fluorobenzaldehyde and 0.2 g of tetrabutylammonium bromide at 20°-25° C., whilst stirring, and the mixture was then stirred at 20°-25° C. for 4 hours. 100 ml of toluene were then added to the reaction mixture and the mixture was extracted twice by shaking with 60 ml of water each time. The organic phase was separated off and dried over magnesium sulphate and the solvent was distilled off under a waterpump vacuum. Last residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 4.4 g (77% of theory) of (+)-trans-Z-3-(2-chloro-2-(4-chloro-phenyl)vinyl)-2,2-dimethyl-cyclopropane-carboxylic acid (±)-α-cyano-3-phenoxy-4-fluoro-benzyl ester were obtained as a viscous oil with an optical rotation [α]D of +58.2° (C=100 mg in 10 ml of CHCl3).

Workup

  1. stirringthe mixture was then stirred at 20°-25° C. for 4 hours
  2. extractionthe mixture was extracted twice
  3. stirringby shaking with 60 ml of water each time
  4. customThe organic phase was separated off
  5. dry with materialdried over magnesium sulphate
  6. distillationthe solvent was distilled off under a waterpump vacuum
  7. customLast residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg

Sources & evidence

ORD record
ord-a7620ee028bc454fb53328517de23e9e
Source dataset
uspto-grants-1988_09
Patent number
US04772629

Reaction notes

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