1-Bromo-4-fluorobenzene → HCID 86748592, compound

HRID 1609431Notes

Reaction equation

HRID 1609431 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC1C=CC(Br)=CC=1.[F:28][C:29]1[CH:37]=[CH:36][C:32]([CH2:33][CH2:34]O)=[CH:31][CH:30]=1.[Br-].FC1C=CC(CC[P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:67]([CH:72]1[CH2:77][CH2:76][CH:75]([CH2:78][CH:79]=O)[CH2:74][CH2:73]1)[CH2:68][CH2:69][CH2:70][CH3:71]>CCOCC.O1CCCC1.C1(C)C(C)=CC=CC=1>[F:28][C:29]1[CH:37]=[CH:36][C:32](/[CH:33]=[CH:34]\[CH2:79][CH2:78][CH:75]2[CH2:76][CH2:77][CH:72]([CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])[CH2:73][CH2:74]2)=[CH:31][CH:30]=1

Participants

9

Reactant 5

HCID 99931-Bromo-4-fluorobenzeneHCID 11776TriphenylphosphineHCID 820684-Fluorophenethyl AlcoholHCID 139990854-PentylcyclohexaneacetaldehydeHCID 223867454-Fluorophenethyltriphenylphosphonium bromide

Product 1

HCID 86748592HCID 86748592, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a flask, were placed triphenylphosphine (2.9 g, 11 mmol) and 4-fluorophenyl bromide (2.2 g, 11 mmol) prepared from 4-fluorophenethyl alcohol, followed by adding and dissolving xylene (5 ml), heating under reflux for 10 hours, depositing and filtering off white crystals (4.6 g, 10 mmol) of 4-fluorophenethyltriphenylphosphonium bromide. After drying, the white crystals were dissolved in tetrahydrofuran (THF, 10 ml), followed by stirring under ice cooling, adding a hexane solution (1.6M, 6.1 ml) of n-butyl lithium dropwise; stirring at room temperature for 2 hours, adding THF (5 ml) solution of 4-pentylcyclohexylacetaldehyde (2.1 g, 11 mmol), further stirring for 5 hours, adding ether after the completion of reaction. After separating the deposited white crystals by filtration, the filtrate was concentrated under reduced pressure, purifying the resulting oily substance by means of silica gel column chromatography, to obtain a mixture (2.2 g, 7.3 mmol) of 1-(4-fluorophenyl)-4-(4pentylcyclohexyl)-2Z-butene with its E-isomer.

Workup

  1. customInto a flask, were placed
  2. additionby adding
  3. temperatureheating
  4. temperatureunder reflux for 10 hours
  5. customAfter drying
  6. dissolutionthe white crystals were dissolved in tetrahydrofuran (THF, 10 ml)
  7. additionadding a hexane solution (1.6M, 6.1 ml) of n-butyl lithium dropwise
  8. stirringstirring at room temperature for 2 hours
  9. stirringfurther stirring for 5 hours
  10. customafter the completion of reaction
  11. customAfter separating the deposited white crystals
  12. filtrationby filtration
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. custompurifying the resulting oily substance by means of silica gel column chromatography

Sources & evidence

ORD record
ord-89529f1a685c4259b28b992a5964a8ce
Source dataset
uspto-grants-1995_03
Patent number
US05401434

Reaction notes

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