Triphenylphosphine → 1-Bromo-4-(p-chlorophenyl)-2-fluoro-4-methyl-2-pentene
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:36])([CH3:35])[CH:30]=[C:31]([F:34])[CH2:32]O)=[CH:25][CH:24]=1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:32][C:31]([F:34])=[CH:30][C:29]([C:26]1[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=1)([CH3:36])[CH3:35]Participants
Procedure
Under a nitrogen atmosphere, a solution of triphenyl phosphine (0.96 g, 4.25 mmol) in carbon tetrachloride at −5° C. is treated dropwise with a solution of bromine (0.679 g, 4.25 mmol) in carbon tetrachloride, warmed to and stirred at room temperature for 45 minutes, treated with a solution of 4-(p-chlorophenyl)-2-fluoro-4-methyl-2-penten-1-ol, (Z)—(0.81 g, 3.54 mmol) in carbon tetrachloride, refluxed for 2 hours, cooled to room temperature, and poured into petroleum ether. The resultant mixture is filtered through diatomaceous earth. The filtrate is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain an oil. Flash column chromatography of the oil using silica gel and a 1:9 ethyl acetate/hexanes solution gives the title product as a colorless oil (0.736 g, 71% yield) which is identified by NMR spectral analyses.
Workup
- temperaturewarmed to and
- temperaturecooled to room temperature
- filtrationThe resultant mixture is filtered through diatomaceous earth
- washThe filtrate is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customto obtain an oil
Sources & evidence
- ORD record
- ord-4d13f5869fb14839be54002baccf8943
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06262319B1
Reaction notes
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