Fluretofene → 4'-Ethenyl-2-fluoro-1,1'-biphenyl

HRID 2398319Notes

Reaction equation

HRID 2398319 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])=[CH:5][CH:4]=1)#[CH:2].[H][H]>[Pd].N1C=CC=CC=1>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[CH2:2])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 42040FluretofeneHCID 178418361HCID 178418361, compound

Product 1

HCID 194261784'-Ethenyl-2-fluoro-1,1'-biphenyl

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

1-Ethynyl-4-(2-fluorophenyl)benzene, 29.6 g., was reduced in a Parr Instrument Company Series 3910 Low-Pressure Shaker-Type Apparatus, using 450 ml. of pyridine, and 0.3 g. of 5 percent palladium on barium sulfate; reduction was carried out at room temperature for 30 minutes and at an initial hydrogen pressure of 30 psig. The reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was vacuum distilled to give 20.5 g. of solid which was recrystallized from methanol to give 4-(2-fluorophenyl)-1-vinylbenzene, mp 38° . The material contained traces of pyridine and 1-ethyl-4-(2-fluorophenyl)benzene, as shown by nuclear magnetic resonance analysis. The following elemental analysis was obtained:

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. distillationdistilled
  4. customto give 20.5 g
  5. customof solid which was recrystallized from methanol

Sources & evidence

ORD record
ord-4faf20f675ff4a92b5154a4768bc0afb
Source dataset
uspto-grants-1977_05
Patent number
US04024284

Reaction notes

Loading…