Triphenylphosphine → (1S,2S,5S)-2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]heptane
Reaction equation
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]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
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.
Workup
- 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
Sources & evidence
- ORD record
- ord-a7bbb33d8fbd4d458dd121458357d148
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05294638
Reaction notes
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