Hydrofluoric Acid → 3,4,5,2'-Tetrafluoro-4'-(4-fluoro-4-propylcyclohexyl)-biphenyl

HRID 1106372Notes

Reaction equation

HRID 1106372 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][C:19](=[CH:22][CH2:23][CH3:24])[CH2:18][CH2:17]3)=[CH:12][C:11]=2[F:25])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[FH:26].C(=O)([O-])O.[Na+]>ClCCl.N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:17][CH2:18][C:19]([F:26])([CH2:22][CH2:23][CH3:24])[CH2:20][CH2:21]3)=[CH:12][C:11]=2[F:25])[CH:5]=[C:6]([F:9])[C:7]=1[F:8]

Participants

6

Reactant 3

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 187879283,4,5,2'-Tetrafluoro-4'-(4-propylidenecyclohexyl)biphenyl

Product 1

HCID 187879303,4,5,2'-Tetrafluoro-4'-(4-fluoro-4-propylcyclohexyl)-biphenyl

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-25 °C

Procedure

8.0 g of 3,4,5,2'-tetrafluoro-4'-(4-propylidenecyclohexyl)biphenyl in 16 ml of dichloromethane were introduced into a Teflon apparatus and cooled to -25° C. 80 ml of a 70% solution of hydrogen fluoride in pyridine were then added dropwise with stirring, and the mixture was stirred for 30 minutes at -25° C. and then for a further 1 hour at room temperature. The reaction solution was poured into a suspension of 10 g of sodium hydrogencarbonate and 200 g of ice-water. The mixture was then extracted with 3×80 ml of hexane. The combined organic extracts were washed once with 50 ml of sodium chloride solution, dried using sodium sulfate, filtered and evaporated to a residue. The crude product was purified by means of a silica-gel frit and the eluate was evaporated to a residue, giving 3,4,5,2'-tetrafluoro-4'-(4-fluoro-4-propylcyclohexyl)-biphenyl (C 73 N (48.8) I, Δε=15.3, Δn=+0.111).

Workup

  1. stirringthe mixture was stirred for 30 minutes at -25° C.
  2. extractionThe mixture was then extracted with 3×80 ml of hexane
  3. washThe combined organic extracts were washed once with 50 ml of sodium chloride solution
  4. customdried
  5. filtrationfiltered
  6. customevaporated to a residue
  7. customThe crude product was purified by means of a silica-gel frit
  8. customthe eluate was evaporated to a residue

Sources & evidence

ORD record
ord-92568cb6a80f4bd7bbe8dfa4e7e8aad5
Source dataset
uspto-grants-2000_05
Patent number
US06057006

Reaction notes

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