Ethyl m-toluate → Ethyl 3-(bromomethyl)benzoate

HRID 1763689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1763689
[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:2]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:1]1[CH:2]=[C:3]([CH:4]=[CH:5][CH:6]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Komponenten

4

Edukt 2

HCID 67117Ethyl m-toluateHCID 67184N-bromobutanimide

Produkt 1

HCID 10857675Ethyl 3-(bromomethyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

Compound XIII is prepared by the following series of reactions: (1) ethyl m-toluate is brominated with N-bromosuccinimide in CCl4 to give ethyl 3-bromomethylbenzoate; (2) the bromo compound is treated with sodio bis-tert-butyl malonate and the product heated in toluene with a catalystic amount of a strong acid (preferably p-toluene-sulfonic acid) to effect elimination and decarboxylation and afford m-ethoxycarbonylhydrocinnamic acid; (3) the latter compound is made to react with thionyl chloride and the resulting acid chloride is reduced with potassium or sodium borohydride to yield ethyl 3-(3-hydroxypropyl)-benzoate; (4) the hydroxy ester is treated with phosphorus tribromide is ether to give reagent XIII.

Quellen und Nachweise

ORD-Eintrag
ord-a20d4ade3de2483d8d4000213d584140
Quelldatensatz
uspto-grants-1978_09
Patentnummer
US04112236

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