Water → 5-(Bromomethyl)-3-(4-chloro-2-methoxyphenyl)-1,2,4-thiadiazole
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH2:13]O)[S:10][N:9]=2)=[C:4]([O:15][CH3:16])[CH:3]=1.P(Br)(Br)[Br:18].O>C1(C)C=CC=CC=1>[Br:18][CH2:13][C:11]1[S:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[O:15][CH3:16])[N:12]=1Komponenten
5
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
To a solution of (3-(4-chloro-2-methoxyphenyl)-1,2,4-thiadiazol-5-yl)methanol (0.08 g, 0.31 mmol) in toluene (4 ml) was added PBr3 (49 μl, 0.47 mmol) and the resulting reaction mixture was heated at 60° C. for 2 h. After the completion of the reaction (TLC monitoring), the reaction mixture was cooled to 0° C., added water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organics was washed with saturated NaHCO3 solution, dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified over silica gel (100-200 M, 5% EtOAc-Hexane) to get the desired product (0.063 g, 64%). MS: 319 (M+H)+.
Aufarbeitung
- customthe resulting reaction mixture
- customAfter the completion of the reaction (TLC monitoring)
- temperaturethe reaction mixture was cooled to 0° C.
- extractionextracted with ethyl acetate (3×50 ml)
- washThe combined organics was washed with saturated NaHCO3 solution
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe crude residue was purified over silica gel (100-200 M, 5% EtOAc-Hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-8ad3327282d046898f49098c9cd5add3
- Quelldatensatz
- uspto-grants-2013_07
- Patentnummer
- US08492414B2
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