Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | 4-Fluoro-3-phenoxybenzaldehyde | HCID 110068 | — |
| Reactant | HCID 54563404 | HCID 54563404 | — |
| Catalyst | Tetrabutylammonium Bromide | HCID 74236 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 54064235 | HCID 54064235 | 70.3% |
Reaction Steps
4.32 g (0.02 mol) of 3-phenoxy-4-fluoro-benzaldehyde and 6.96 g (0.02 mol) of 2,2-dimethyl-3-(2-bromo-2-(4-chlorophenyl)-vinyl)-cyclopropanecarboxylic acid chloride were together added dropwise to a mixture of 1.6 g of sodium cyanide, 2.5 ml of water, 100 ml of n-hexane and 0.5 g of tetrabutylammonium bromide at 20°-25° C., while stirring, and the mixture was then stirred at 20°-25° C. for 4 hours. 300 ml of toluene were then added to the reaction mixture and the mixture was extracted by shaking twice with 300 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. 7.8 g (70.3% of theory) of 2,2-dimethyl-3-(2-bromo-2-(4-chloro-phenyl)-vinyl)-cyclopropanecarboxylic acid 3-phenoxy-4-fluoro-α-cyano-benzyl ester were obtained as a viscous oil. The structure was confirmed by the 1H-NMR spectrum.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04279920 |
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| Source dataset | uspto-grants-1981_07 |
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| ORD ID | ord-55975649e6a3405fb7c963e980b7757d |
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| Source note | uspto-grants-1981_07 |
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