Triphenylphosphine → HCID 86748595, compound

HRID 1609435Notes

Reaction equation

HRID 1609435 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:2]=1.[F:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[Br:30])[CH2:24][CH2:25]Br.FC1C=C(C=CC=1Br)CCO.CC(C)([O-])C.[K+].C([C:50]1([CH:56]2[CH2:61][CH2:60][CH:59]([CH2:62][CH:63]=O)[CH2:58][CH2:57]2)[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]1)C>CCOCC.C1COCC1.C1(C)C(C)=CC=CC=1>[F:20][C:21]1[CH:22]=[C:23](/[CH:24]=[CH:25]\[CH2:63][CH2:62][CH:59]2[CH2:58][CH2:57][CH:56]([CH:50]3[CH2:51][CH2:52][CH:53]([CH2:1][CH3:2])[CH2:54][CH2:55]3)[CH2:61][CH2:60]2)[CH:27]=[CH:28][C:29]=1[Br:30]

Participants

9

Reactant 5

HCID 11776TriphenylphosphineHCID 20081205Benzeneethanol, 4-bromo-3-fluoro-HCID 200812081331944-02-5HCID 23665647Potassium tert-butoxideHCID 54176917HCID 54176917, compound

Product 1

HCID 86748595HCID 86748595, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Into a flask, were placed triphenylphosphine (2.9 g, 11 mmol) and 3-fluoro-4-bromophenethylbromide (2.2 g, 11 mmol) prepared from 3-fluoro-4-bromophenethylalcohol, followed by adding and dissolving xylene (15 ml), heating under reflux for 10 hours, adding THF (10 ml) to the reaction solution and stirring under ice-cooling, adding potassium-t-butoxid (1.1 g, 10 mmol) slowly to the reaction solution, stirring the reaction solution after the completion of dropping at room temperature for 2 hours, adding THF (10 ml) solution of 4-(ethylcyclohexyl) cyclohexylacetoaldehyde (2.4 g, 10 mmol), further stirring for 5 hours, adding ether after the completion of reaction, filtering off white solid deposited, concentrating the filtrate under reduced pressure, purifying the obtained brown oil by means of silica gel chromatography, to obtain a mixture (1.8 g, 4.2 mmol) of 1-(3-fluoro-4-bromophenyl)-4-(4-(4-ethylcyclohexyl)cyclohexyl)-2-Z-butene with its E-isomer.

Workup

  1. customInto a flask, were placed
  2. additionby adding
  3. temperatureheating
  4. temperatureunder reflux for 10 hours
  5. temperaturecooling
  6. stirringstirring the reaction solution after the completion
  7. stirringfurther stirring for 5 hours
  8. customafter the completion of reaction
  9. filtrationfiltering off white solid
  10. concentrationconcentrating the filtrate under reduced pressure
  11. custompurifying the obtained brown oil by means of silica gel chromatography

Sources & evidence

ORD record
ord-12f8f418c13b4e889771525d3b33c7bf
Source dataset
uspto-grants-1995_03
Patent number
US05401434

Reaction notes

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