Water → HCID 23432345, Verbindung

HRID 2121300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2121300
B(Br)(Br)Br.[C:5]([C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)#[N:6].O>ClCCl>[C:5]([C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)#[N:6]

Komponenten

5

Edukt 3

HCID 962WaterHCID 25134Boron tribromideHCID 154458915-(4-Methoxyphenyl)thiophene-2-carbonitrile

Produkt 1

HCID 23432345HCID 23432345, VerbindungAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A 1M solution of boron tribromide in dichloromethane (55 cm3) was added dropwise to a solution of 2-cyano-5-(4-methoxyphenyl)thiophene (2.3 g) and dichloromethane (80 cm3) at 0° C. under an atmosphere of nitrogen. The reaction solution was stirred overnight and water (100 cm3) added. The organic layer was separated off and the aqueous layer extracted with dichloromethane (2×100 cm3). The combined organic layers were washed with brine (2×100 cm3) and then dried (MgSO4), filtered and evaporated down. The residue was purified by column chromatography on silica gel using a 9:1 hexane/ethyl acetate mixture as eluent and recrystallisation from ethanol to yield 1.4 g of g 2-cyano-5-(4-hydroxyphenyl)thiophene.

Aufarbeitung

  1. customThe organic layer was separated off
  2. extractionthe aqueous layer extracted with dichloromethane (2×100 cm3)
  3. washThe combined organic layers were washed with brine (2×100 cm3)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated down
  7. customThe residue was purified by column chromatography on silica gel using a 9:1 hexane/ethyl acetate mixture as eluent
  8. customrecrystallisation from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-a91f7e5a53e84296b2ff195c3862d232
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06696110B1

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