Water → HCID 86738077, compound

HRID 848771Notes

Reaction equation

HRID 848771 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[F:16])[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:17]/[C:18](/[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)=[CH:19]\[C@H:20]1[C@H:22]([C:23](Cl)=[O:24])[C:21]1([CH3:27])[CH3:26].[C-:35]#[N:36].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.CCCCCC>[C:35]([CH:11]([O:12][C:23]([C@H:22]1[C@H:20](/[CH:19]=[C:18](\[Cl:17])/[C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[C:21]1([CH3:27])[CH3:26])=[O:24])[C:10]1[CH:13]=[CH:14][C:15]([F:16])=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1)#[N:36]

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 70.6%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

1.08 g (0.005 mol) of 3-phenoxy-4-fluoro-benzaldehyde and 1.52 g (0.005 mol) of (±)-trans-3-(Z-2-chloro-2-(4-chlorophenyl)-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid chloride were together added dropwise to a mixture of 0.4 g of sodium cyanide, 0.6 ml of water, 20 ml of n-hexane and 0.1 g of tetrabutylammonium bromide at 20°-25° C., whilst stirring, and the reaction mixture was then stirred at 20°-25° C. for 4 hours. 100 ml of toluene were subsequently added and the reaction mixture was extracted twice by shaking with 60 ml of water each time. The organic phases were 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. 1.8 g (70.6% of theory) of (±)-trans-3-(Z-2-chloro-2-(4-chlorophenyl)-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid (±)-α-cyano-3-phenoxy-4-fluoro-benzyl ester were obtained as a viscous oil. The structure was confirmed by the 1H-NMR spectrum.

Workup

  1. stirringthe reaction mixture was then stirred at 20°-25° C. for 4 hours
  2. extractionthe reaction mixture was extracted twice
  3. stirringby shaking with 60 ml of water each time
  4. customThe organic phases were 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-4e64c9ded7914e5bb5625f0e5ba13506
Source dataset
uspto-grants-1981_10
Patent number
US04297371

Reaction notes

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