Toluene → 2-(Bromomethyl)-5-nitrothiophene

HRID 861881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 861881
P(Br)(Br)[Br:2].O[CH2:6][C:7]1[S:8][C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=1.C1(C)C=CC=CC=1>O>[Br:2][CH2:6][C:7]1[S:8][C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 24614Phosphorus tribromideHCID 332588(5-nitrothiophen-2-yl)methanol

Produkt 1

HCID 536851562-(Bromomethyl)-5-nitrothiopheneAusbeute 261,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Phosphorus tribromide (PBr3) (10.45 g) was added dropwise to a mixture of 2-hydroxymethyl-5-nitrothiophene (17.7 g) and toluene (150 ml) and this mixture was stirred at 70° C. for 1.5 hours. The reaction mixture was poured into water and extracted with ether. The ether layer was washed with water and dried (MgSO4), after which the solvent was evaporated off. The residual oil was subjected to solica gel column chromatography and eluted with chloroform to yield 2-bromomethyl-5-nitrothiophene (22.43 g, 92%) as an oil.

Aufarbeitung

  1. extractionextracted with ether
  2. washThe ether layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customafter which the solvent was evaporated off
  5. washeluted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-98cdb1d533454e5390c0078761500449
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716944

Notizen zur Reaktion

Wird geladen…