Reaktion #487537

Reaktionsgleichung

1-Bromo-2-fluorobenzene

pent-4-yn-1-ol

→

5-(2-fluorophenyl)pent-4-yn-1-ol

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was heated
2. 2
   Temperaturat reflux for 16 hours
3. 3
   TemperaturThe solution was cooled
4. 4
   Filtrationfiltered through Celite
5. 5
   Waschenthe Celite pad rinsed with EtOAc
6. 6
   Sonstigethe solvent removed by rotoevaporation

Vorschrift

1-Bromo-2-fluorobenzene [1072-85-1](3.0 g, 17 mmol, 1.0 equiv) and pent-4-yn-1-ol [5390-04-5](2.3 mL, 25 mmol, 1.5 equiv) were dissolved in acetonitrile (40 mL). CuI (0.13 g, 0.68 mmol, 0.04 equiv) and TEA (3.4 mL, 25 mmol, 1.5 equiv) was added to the stirred solution followed by tetrakis(triphenylphosphine)palladium(O) (0.39 g, 0.34 mmol, 0.02 equiv). The solution was heated at reflux for 16 hours. The solution was cooled, filtered through Celite, the Celite pad rinsed with EtOAc and the solvent removed by rotoevaporation. Column chromatography (9:1 hexanes:ethyl acetate) of the residue afforded pure 5-(2-fluorophenyl)pent-4-yn-1-ol Intermediate 60 (1.3 g, 43%). 1H NMR (600 MHz, DMSO-d6) δ: 7.42 (t, J=7.48 Hz, 1H), 7.38-7.32 (m, 1H), 7.22 (t, J=9.10 Hz, 1H), 7.14 (t, J=7.56 Hz, 1H), 4.50 (t, J=5.21 Hz, 1H), 3.49 (q, J=5.92 Hz, 2H), 2.47 (t, J=7.12 Hz, 2H), 1.66 (quin, J=6.68 Hz, 2H).

Quelle