Реакция #487537

Уравнение реакции

1-Bromo-2-fluorobenzene

pent-4-yn-1-ol

→

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

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   ТемператураThe solution was heated
2. 2
   Температураat reflux for 16 hours
3. 3
   ТемператураThe solution was cooled
4. 4
   Фильтрацияfiltered through Celite
5. 5
   Промывкаthe Celite pad rinsed with EtOAc
6. 6
   Другоеthe solvent removed by rotoevaporation

Методика

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).

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