Triphenylphosphine → 2-Methoxycarbonylthiophen-3-ylmethyltriphenylphosphonium bromide

HRID 1831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1831
[Br:1][CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([O:10][CH3:11])=[O:9].[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[Br-:1].[CH3:11][O:10][C:8]([C:4]1[S:5][CH:6]=[CH:7][C:3]=1[CH2:2][P+:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 10537693Methyl 3-(bromomethyl)thiophene-2-carboxylate

Produkt 1

HCID 196930522-Methoxycarbonylthiophen-3-ylmethyltriphenylphosphonium bromideAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-bromomethyl-2-thiophenecarboxylate (7.31 g, 31.1 mmol) in toluene (90 ml) was added triphenylphosphine (7.92 g, 30.2 mmol) under ice cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 2 days. The precipitated crystals were collected by filtration and dried to give 2-methoxycarbonylthiophen-3-ylmethyltriphenylphosphonium bromide (10.57 g, 70.4%). This product was subjected to the reaction of Reference Example 13 without purification.

Aufarbeitung

  1. filtrationThe precipitated crystals were collected by filtration
  2. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f5ea82e1d125454e8bce94b7fc33917f
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726325

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