N-bromobutanimide → 2-(Bromomethyl)thiophene-3-carbonitrile

HRID 1251178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1251178
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]#[N:8].[Br:9]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:9][CH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]#[N:8]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 125657872-Methylthiophene-3-carbonitrile

Produkt 1

HCID 225036202-(Bromomethyl)thiophene-3-carbonitrileAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-Methyl-3-cyanothiophene (2.108 g) was dissolved in benzene (30 ml), followed by the addition of N-bromosuccinimide (4.8 g) and 70% benzoyl peroxide (202 mg), and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was cooled, and the resulting precipitates were filtered off. Then the filtrate was diluted with ethyl acetate, washed with an aqueous solution of saturated sodium bicarbonate, dried (over MgSO4) and then evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a yellow oil (2.746 g, yield; 82%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customthe resulting precipitates
  3. filtrationwere filtered off
  4. additionThen the filtrate was diluted with ethyl acetate
  5. washwashed with an aqueous solution of saturated sodium bicarbonate
  6. dry with materialdried (over MgSO4)
  7. customevaporated
  8. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Quellen und Nachweise

ORD-Eintrag
ord-79adb296255f4eb89e315f2b1e037f1a
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06340759B1

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