反応 #48043

反応方程式

1-(4-bromophenyl)-cyclobutanol

triethylsilane

→

1-bromo-4-cyclobutyl-benzene

収率 66.3%

溶媒

DCM

反応条件

後処理

1. 1
   workup.ADDITIONThen 1.15 ml of boron trifluoride diethyl etherate complex were added
2. 2
   温度the reaction mixture was warmed to −40° C.
3. 3
   その他The reaction was then quenched by addition of 10% aqueous KHCO3
4. 4
   抽出the mixture was extracted three times with DCM
5. 5
   洗浄The combined extracts were washed with brine
6. 6
   乾燥dried with magnesium sulfate
7. 7
   濃縮concentrated
8. 8
   その他The remaining residue was purified by column chromatography (silica gel; cyclohexane)

実験手順

To a solution of 1.37 g of 1-(4-bromophenyl)-cyclobutanol (6 mmol) in 15 ml DCM were added 1.15 ml of triethylsilane (7.2 mmol) and the mixture was cooled to −78° C. Then 1.15 ml of boron trifluoride diethyl etherate complex were added and the reaction mixture was warmed to −40° C. and stirred for 8 h. The reaction was then quenched by addition of 10% aqueous KHCO3 and the mixture was extracted three times with DCM. The combined extracts were washed with brine, dried with magnesium sulfate and concentrated. The remaining residue was purified by column chromatography (silica gel; cyclohexane) to give 0.84 g (66%) of 1-bromo-4-cyclobutyl-benzene as a colorless liquid. 1H NMR (CDCl3, 300 MHz): δ 1.85 (m, 1H), 1.92-2.18 (m, 3H), 2.33 (m, 2H), 3.49 (quint, J=8.5 Hz, 1H), 7.08 (d, J=8.5 Hz, 2H), 7.40 (d, J=8.5 Hz, 2H).

出典