Water → 3,4,5,2'-Tetrafluoro-4'-(4-propylidenecyclohexyl)biphenyl

HRID 1106371Notes

Reaction equation

HRID 1106371 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[C:15]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([F:23])[CH:16]=1.[Br-].[CH2:25]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:26][CH3:27].CC(C)([O-])C.[K+].O>C1COCC1>[F:23][C:17]1[CH:16]=[C:15]([C:3]2[CH:4]=[CH:5][C:6]([CH:8]3[CH2:13][CH2:12][C:11](=[CH:25][CH2:26][CH3:27])[CH2:10][CH2:9]3)=[CH:7][C:2]=2[F:1])[CH:20]=[C:19]([F:21])[C:18]=1[F:22]

Participants

6

Reactant 4

HCID 962WaterHCID 80374Propyltriphenylphosphonium bromideHCID 18787931HCID 18787931, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 187879283,4,5,2'-Tetrafluoro-4'-(4-propylidenecyclohexyl)biphenyl

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

12.5 g of 4-(2,3',4',5'-tetrafluorobiphenyl-4-yl)cyclohexanone and 15.5 g of propyltriphenylphosphonium bromide were introduced into 150 ml of THF, and the mixture was cooled to -10° C. with stirring and under nitrogen. A solution of 4.5 g of potassium tert-butoxide in 150 ml of THF was then added dropwise with stirring at -10° C., and the mixture was then stirred at room temperature for a further 2 hours. The yellow suspension was then cooled to 10° C., and 200 ml of water were added. The organic phase was separated off, and the aqueous phase was extracted once with 100 ml of methyl tert-butyl ether. The combined organic extracts were washed once with 50 ml of water, dried using sodium sulfate, filtered and evaporated to a residue. The residue 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-propylidenecyclohexyl)bi-phenyl.

Workup

  1. stirringwith stirring at -10° C.
  2. stirringthe mixture was then stirred at room temperature for a further 2 hours
  3. temperatureThe yellow suspension was then cooled to 10° C.
  4. customThe organic phase was separated off
  5. extractionthe aqueous phase was extracted once with 100 ml of methyl tert-butyl ether
  6. washThe combined organic extracts were washed once with 50 ml of water
  7. customdried
  8. filtrationfiltered
  9. customevaporated to a residue
  10. customThe residue was purified by means of a silica-gel frit
  11. customthe eluate was evaporated to a residue

Sources & evidence

ORD record
ord-50d72c6f8c494d9fa22cc3e54102718b
Source dataset
uspto-grants-2000_05
Patent number
US06057006

Reaction notes

Loading…