Water → 4'-(trans-4-Propylcyclohexyl)-3,4-difluorobiphenyl

HRID 1181

Reaction equation

HRID 1181 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([Si](OC)(OC)OC)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-].[F:41][C:42]1[CH:43]=[C:44](Br)[CH:45]=[CH:46][C:47]=1[F:48].O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:45]3[CH:44]=[CH:43][C:42]([F:41])=[C:47]([F:48])[CH:46]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 676754-Bromo-1,2-difluorobenzeneHCID 2724141Tetrabutylammonium FluorideHCID 108602534-(4-Propylcyclohexyl)-phenyltrimethoxysilane

Product 1

HCID 6123064'-(trans-4-Propylcyclohexyl)-3,4-difluorobiphenylYield 94.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent3×

Procedure

To 0.645 g (2 mmol) of 4-(4-propylcyclohexyl)-phenyltrimethoxysilane (Ih) was added 2.1 ml of TBAF (2.1 mmol, 1M in THF) under nitrogen, and the mixture was stirred at room temperature for 30 minutes. After the solvent was removed under reduced pressure, a solution of 3,4-difluorobromobenzene (0.463 g, 2.4 mmol) in toluene (1 ml) was added, followed by the addition of a suspension of tetrakis(triphenylphosphine)palladium(0) (0.116 g, 0.1 mmol) in toluene (3 ml). The resulting mixture was refluxed for 3 hours. After cooling, to the reaction mixture were added water and toluene. The organic layer was separated and the aqueous layer was extracted with toluene three times. The combined organic layer was dried over magnesium sulfate. After the magnesium sulfate was removed by filtration, the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (heptane) to obtain 0.594 g (40%) of white crystals.

Workup

  1. customAfter the solvent was removed under reduced pressure
  2. temperatureThe resulting mixture was refluxed for 3 hours
  3. temperatureAfter cooling, to the reaction mixture
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with toluene three times
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. customAfter the magnesium sulfate was removed by filtration
  8. customthe filtrate was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (heptane)

Sources & evidence

ORD record
ord-f5c19c1716b641f7a3721e4238a2fc65
Source dataset
uspto-grants-1998_03
Patent number
US05723621

Linked notes

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