Reacción #487537

Ecuación de reacción

1-Bromo-2-fluorobenzene

pent-4-yn-1-ol

→

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

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe solution was heated
2. 2
   Temperaturaat reflux for 16 hours
3. 3
   TemperaturaThe solution was cooled
4. 4
   Filtraciónfiltered through Celite
5. 5
   Lavadothe Celite pad rinsed with EtOAc
6. 6
   Otrothe solvent removed by rotoevaporation

Procedimiento

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).

Fuente