Triphenylphosphine → Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromide

HRID 443663Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 443663
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C(C)=CC=CC=1>[Br-:1].[CH3:9][O:8][C:6]([C:5]1[CH:4]=[C:3]([CH:12]=[CH:11][CH:10]=1)[CH2:2][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:7]

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 517981Methyl 3-(bromomethyl)benzoate

Produkt 1

HCID 10051285Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

The preparation of XIII begins with the known methyl 3-(bromomethyl)benzoate. This halide is heated in xylene solution with triphenylphosphine to yield (3-methoxycarbonylbenzyl)triphenylphosphonium bromide. The phosphonium salt is converted to the ylide with sodium ethoxide in ethanol and the ylide caused to react with acetaldehyde to yield ethyl 3-(1-propenyl)benzoate. [Note that the ethyl ester has been obtained as a result of transesterification with solvent ethanol.] The ester is heated with N-bromosuccinimide in carbon tetrachloride for an extended period to yield ethyl 3-(3-bromo-1-propenyl)benzoate. This compound is treated with the anion derived from methyl methylthiomethyl sulfoxide as described in previous examples. The resulting dimethyl mercaptal S-oxide is hydrolyzed with acid catalysis to the aldehyde reagent XIII.

Quellen und Nachweise

ORD-Eintrag
ord-e0b73fd41af54dd9b395a80854874a20
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04260771

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