Sulfuric Acid → Methyl 2-(2-[4-fluorophenyl]ethyl)phenylacetate

HRID 1885800

Reaktionsgleichung

Reaktionsgleichung von HRID 1885800
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[Br-].COC(C1C=CC=CC=1C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O.O1C=CC=C1C[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[CH2:54][C:55]([O:57][CH3:58])=[O:56].C(Cl)C1C=CC=CC=1.C1(CC([O-])=O)C=CC=CC=1.[C-]#N.[K+].C1(CC#N)C=CC=CC=1.S(=O)(=O)(O)O>CS(C)=O.CO>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[CH2:54][C:55]([O:57][CH3:58])=[O:56])=[CH:4][CH:3]=1

Komponenten

11

Edukt 8

HCID 1118Sulfuric AcidHCID 7503Benzyl ChlorideHCID 8794PhenylacetonitrileHCID 9032Potassium CyanideHCID 680234-FluorobenzaldehydeHCID 4409936PhenylacetateHCID 10743695{[2-(Methoxycarbonyl)phenyl]methyl}(triphenyl)phosphanium bromideHCID 19879669Methyl 2-[2-(2-furyl)ethyl]phenylacetate

Produkt 1

HCID 19879670Methyl 2-(2-[4-fluorophenyl]ethyl)phenylacetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

Methyl 2-(2-[4-fluorophenyl]ethyl)phenylacetate was prepared from 4-fluorobenzaldehyde and (o-methoxycarbonylbenzyl)triphenylphosphonium bromide by a route similar to that described in Example 3 for the preparation of methyl 2-[2-(2-furyl)ethyl]phenylacetate. In this instance, the benzyl chloride was converted into the phenylacetate by treatment with potassium cyanide in DMSO and, then, methanolysis of the resulting phenylacetonitrile with sulphuric acid in methanol.

Quellen und Nachweise

ORD-Eintrag
ord-51a733eb0d084f3f86d134e975174bbe
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05145954

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