Reaktion #69860

Reaktionsgleichung

(2-iodophenyl)methanol

1H-1,2,3-triazole

Cs2CO3

→

title compound

Ausbeute 130.0%

(2-(2H-1,2,3-triazol-2-yl)phenyl)methanol

Ausbeute 130.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   TemperaturThe reaction mixture was cooled to rt
3. 3
   Filtrationfiltered
4. 4
   Sonstigeto remove the solids
5. 5
   EinengenThe filtrate was concentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane)

Vorschrift

To a mixture of (2-iodophenyl)methanol [5159-41-1] (1.50 g, 6.41 mmol), 1H-1,2,3-triazole (0.797 g, 11.54 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine [68737-65-5] (0.091 g, 0.641 mmol) and Cs2CO3 (3.76 g, 11.54 mmol) in DMF (15 mL), CuI (0.61 g, 3.20 mmol) was added and the reaction mixture was stirred for 20 min at 120° C. and 15 min at 160° C. in the microwave. The reaction mixture was cooled to rt and filtered to remove the solids. The filtrate was concentrated under reduced pressure. The residue was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane) to yield the title compound (1.46 g, 64%). [1H NMR (400 MHz, DMSO-d6) ♀ ppm 8.10 (s, 2H), 7.74 (d, J=7.53 Hz, 1H), 7.61 (dd, J=8.03, 1.25 Hz, 1H), 7.52 (td, J=7.53, 1.25 Hz, 1H), 7.44 (m, 1H), 5.26 (t, J=5.40 Hz, 1H), 4.59 (d, J=5.02 Hz, 2H); LCMS RtA=0.68, [M+H]+=176.1].

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