Реакция #9899

Уравнение реакции

NBS

6-cyclobutyl-hexan-1-ol

triphenylphosphine

→

(6-bromo-hexyl)-cyclobutane

Выход 91.3%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Другоеthe reaction was quenched with methanol (0.5 mL)
2. 2
   workup.ADDITIONThe solution was diluted with ether (60 mL)
3. 3
   Промывкаwashed with water, saturated aqueous NaHCO3 and brine successively
4. 4
   ДругоеThe organic layer was dried
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеThe residue was purified by flash chromatography on silica gel
7. 7
   Промывкаeluting with hexane

Методика

To a solution of 6-cyclobutyl-hexan-1-ol (0.47 g, 3.0 mmol) in DMF (10 mL) was added triphenylphosphine (0.88 g, 3.4 mmol). The solution was cooled to 0° C. and NBS (0.57 g, 3.2 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.5 mL). The solution was diluted with ether (60 mL), washed with water, saturated aqueous NaHCO3 and brine successively. The organic layer was dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexane to afford (6-bromo-hexyl)-cyclobutane (0.60 g, 91%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.40 (2H, t, J=6.9 Hz), 2.23 (1H, m), 2.02 (2H, m), 1.82 (4H, m), 1.55 (2H, m), 1.12–1.46 (8H, m); 13C NMR (75 MHz, CDCl3) δ 37.19, 36.39, 34.40, 33.11, 29.07, 28.68, 28.51, 27.26, 18.80.

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