تفاعل #487537

معادلة التفاعل

1-Bromo-2-fluorobenzene

pent-4-yn-1-ol

→

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

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe solution was heated
2. 2
   درجة الحرارةat reflux for 16 hours
3. 3
   درجة الحرارةThe solution was cooled
4. 4
   ترشيحfiltered through Celite
5. 5
   غسيلthe Celite pad rinsed with EtOAc
6. 6
   أخرىthe solvent removed by rotoevaporation

الإجراء التجريبي

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).

المصدر