Triphenylphosphine → (1S,2S,5S)-2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]heptane
반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[CH3:22][C:23]1([CH3:33])[C@H:28]2[CH2:29][C@@H:24]1[CH2:25][CH2:26][C@H:27]2[CH2:30][CH2:31]O>C(#N)C>[CH3:22][C:23]1([CH3:33])[C@H:28]2[CH2:29][C@@H:24]1[CH2:25][CH2:26][C@H:27]2[CH2:30][CH2:31][Br:20]참가 물질
5
반응 조건
- 온도
- 0 °C
실험 절차
15.6 g triphenylphosphine were dissolved in 300 ml acetonitrile, and 3.02 ml bromine were added to the solution in drops with vigorous stirring at a temperature of 0° C. Then a solution of 10 g cisdihydronopol (=2-((1S,2S,5S)6,6-dimethylbicyclo[3,1,1]hept-2-yl)-ethanol) in 100 ml acetonitrile was added, and the reaction mixture was heated to 100° C. (bath temperature) for 5 hours. The reaction mixture was worked up by distilling off the solvent under reduced pressure, and the residue was purified chromatographically over silica gel using dichloromethane as eluent. 12.0 g 2-((1S,2S,5S)-6,6dimethylbicyclo[3,1,1]hept-2-yl)-ethyl bromide were obtained.
후처리
- temperaturethe reaction mixture was heated to 100° C. (bath temperature) for 5 hours
- distillationby distilling off the solvent under reduced pressure
- customthe residue was purified chromatographically over silica gel
출처 및 근거
- ORD 기록
- ord-a7bbb33d8fbd4d458dd121458357d148
- 출처 데이터셋
- uspto-grants-1994_03
- 특허 번호
- US05294638
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