تفاعل #48043

معادلة التفاعل

1-(4-bromophenyl)-cyclobutanol

triethylsilane

→

1-bromo-4-cyclobutyl-benzene

المردود 66.3%

المذيبات

DCM

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر