Carbon tetrabromide → 5-(Bromomethyl)-1,3-diphenyl-1H-1,2,4-triazole

HRID 1621151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1621151
[C:1]1([N:7]2[C:11]([CH2:12]O)=[N:10][C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:40]>ClCCl>[Br:40][CH2:12][C:11]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:10]=1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 132241301,3-Diphenyl-1H-1,2,4-triazole-5-methanol

Produkt 1

HCID 866774905-(Bromomethyl)-1,3-diphenyl-1H-1,2,4-triazoleAusbeute 193,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of (1,3-diphenyl-1H-1,2,4-triazol-5-yl)methanol (350 mg, 1.39 mmol) and triphenylphosphine polymer bound (679 mg, 2.02 mmol) in dichloromethane (6 mL) was added at 0-5° C. carbon tetrabromide (670 mg, 2.02 mmol). The ice bath was removed and the mixture was stirred at RT for 18 h. The suspension was filtered, washed with dichloromethane and evaporated to give 844 mg of yellow oil. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as colorless solid (267 mg, 850 μmol, 61.0%).

Aufarbeitung

  1. customThe ice bath was removed
  2. filtrationThe suspension was filtered
  3. washwashed with dichloromethane
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-75e2a941be7c471d9a3bbe7981e190b1
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772510B2

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