1-Chloro-4-(4-fluorophenyl)-3-butene → 1,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)

HRID 223264Notes

Reaction equation

HRID 223264 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH2:10][CH2:11][Cl:12])=[CH:4][CH:3]=1.[H][H]>[Pd].C(O)(C)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:9][CH2:10][CH2:11][Cl:12])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 542806431-Chloro-4-(4-fluorophenyl)-3-buteneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)Yield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A suspension of 150 g of 4,4-bis-(4-fluorophenyl-3-butenylchloride, 1 l isopropyl alcohol, and 10 g of 10% palladium-on-charcoal was shaken at room temperature under 40 psi of hydrogen. The uptake of hydrogen ceased after about 5 hrs. The mixture was filtered and the solvent was evaporated to provide an oil. Distillation provided 140.2 g (92.8%) of 4,4-bis-(4-fluorophenyl)butylchloride, bp 155°-158° (1.3 mm).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated
  3. customto provide an oil
  4. distillationDistillation

Sources & evidence

ORD record
ord-027879cc2d964f05a60760d1616b6bb9
Source dataset
uspto-grants-1982_10
Patent number
US04352811

Reaction notes

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