반응 #48043

반응 방정식

1-(4-bromophenyl)-cyclobutanol

triethylsilane

→

1-bromo-4-cyclobutyl-benzene

수율 66.3%

용매

DCM

반응 조건

후처리

1. 1
   workup.ADDITIONThen 1.15 ml of boron trifluoride diethyl etherate complex were added
2. 2
   온도the reaction mixture was warmed to −40° C.
3. 3
   기타The reaction was then quenched by addition of 10% aqueous KHCO3
4. 4
   추출the mixture was extracted three times with DCM
5. 5
   세척The combined extracts were washed with brine
6. 6
   건조dried with magnesium sulfate
7. 7
   농축concentrated
8. 8
   기타The remaining residue was purified by column chromatography (silica gel; cyclohexane)

실험 절차

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).

출처