Pyridine → alpha-Cyano-phenylacetic acid pentafluorophenyl ester

HRID 1980229

Reaction equation

[C:1]([CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5])#[N:2].P(Cl)(Cl)(Cl)(Cl)Cl.[F:19][C:20]1[C:25](O)=[C:24]([F:27])[C:23]([F:28])=[C:22]([F:29])[C:21]=1[F:30].N1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.ClCCl>[F:19][C:20]1[C:25]([O:5][C:4](=[O:6])[CH:3]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:1]#[N:2])=[C:24]([F:27])[C:23]([F:28])=[C:22]([F:29])[C:21]=1[F:30]

Participants

Conditions

Temperature: 0 °C

Procedure

8 g. (0.05 moles) of α-cyano-phenylacetic acid are dissolved in 80 ml. of dichloromethane. 10.2 g. (0.05 moles) of phosphorus pentachloride are added and the mixture is stirred for two hours at the boiling point of dichloromethane. The solvent is distilled off and the residue is taken up in carbontetrachloride and the solution is added dropwise to 9.2 g. (0.05 moles) of pentafluorophenol and 4 ml. (0.05 moles) of pyridine-dissolved in 200 ml. of carbontetrachloride. The reaction mixture is cooled to 0° C. and the pyridine chlorohydrate is washed with 2n hydrochloride acid. The organic layer is washed twice with 40 ml. of water, dried over magnesium sulfate and evaporated. The α-cyano-phenylacetic acid-pentafluorophenyl ester is recrystallized from petrolether

Workup

distillationThe solvent is distilled off
additionthe solution is added dropwise to 9.2 g
washthe pyridine chlorohydrate is washed with 2n hydrochloride acid
washThe organic layer is washed twice with 40 ml
dry with materialof water, dried over magnesium sulfate
customevaporated
customThe α-cyano-phenylacetic acid-pentafluorophenyl ester is recrystallized from petrolether

Sources & evidence

ORD record: ord-b008978120024e89b3f15211d4f30f88
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04508658

Linked notes

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