Methyl iodide → 2-(4-Bromophenyl)-4-methoxy-2H-1,2,3-triazole

HRID 709280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 709280
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[N:12]=[C:11]([OH:13])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH2:14]1COCC1.C(=O)([O-])[O-].[Cs+].[Cs+].CI>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[N:12]=[C:11]([O:13][CH3:14])[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 178516800HCID 178516800, Verbindung

Produkt 1

HCID 672492502-(4-Bromophenyl)-4-methoxy-2H-1,2,3-triazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-(4-bromophenyl)-2H-1,2,3-triazol-4-ol (200 mg, 0.833 mmol) was weighed into a 20 ml vial equipped with a septa cap. THF (10.0 ml) was added. To this was added cesium carbonate (814 mg, 2.5 mmol), followed by the addition of methyl iodide (65.8 uL, 1.04 mmol) via syringe. The reaction was heated at 60° C. for 16 hours. Water (20 ml) was added and the product was extracted with ethyl acetate (2×75 ml). Organic phases were combined, dried over potassium carbonate, filtered and concentrated to furnish a light tan solid (190 mg, 89% TY). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.04 (s, 3H) 7.30 (s, 1H) 7.56 (d, J=8.98 Hz, 2H) 7.84 (d, J=8.98 Hz, 2H)

Aufarbeitung

  1. customvial equipped with a septa cap
  2. extractionthe product was extracted with ethyl acetate (2×75 ml)
  3. dry with materialdried over potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto furnish a light tan solid (190 mg, 89% TY)

Quellen und Nachweise

ORD-Eintrag
ord-f35f17ff00ac4e71b206e946a645ac03
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09180123B2

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