4,4'-Bis(1,1-dimethylethyl)-1,1'-biphenyl → [(Z)-1,2-difluoro-2-(4-propylcyclohexyl)vinyl]triethylsilane

HRID 1841831Notes

Reaction equation

HRID 1841831 reaction equation
C(C1C=CC(C2C=CC(C(C)(C)C)=CC=2)=CC=1)(C)(C)C.[Li].Cl[CH:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH2:30][CH3:31])[CH2:25][CH2:24]1.[CH2:32]([Si:34]([CH2:42][CH3:43])([CH2:40][CH3:41])[C:35]([F:39])=[C:36](F)[F:37])[CH3:33]>C1COCC1.O>[F:39]/[C:35](/[Si:34]([CH2:40][CH3:41])([CH2:42][CH3:43])[CH2:32][CH3:33])=[C:36](/[F:37])\[CH:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH2:30][CH3:31])[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 741954,4'-Bis(1,1-dimethylethyl)-1,1'-biphenylHCID 3028194LithiumHCID 109214661,2,2-Trifluoroethenyl-triethylsilaneHCID 199612711-Chloro-4-propylcyclohexane

Product 1

HCID 71074322[(Z)-1,2-difluoro-2-(4-propylcyclohexyl)vinyl]triethylsilane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

74.1 g (0.28 mol) of 4,4′-di-tert-butylbiphenyl are initially introduced in 1000 ml of THF in an argon atmosphere, and 1.6 g (0.23 mol) of lithium (granules) are added at 0° C. After 5 h, the blue solution is cooled to −78° C., and 40.6 g (0.25 mol) of 1-chloro-4-propylcyclohexane are added. After 30 min at this temperature, 49.6 g (0.25 mol) of triethyltrifluorovinylsilane are metered in. The mixture is warmed slowly and stirred at room temperature for 16 h. Water is added, and the batch is extracted with MTBE. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with water and saturated sodium chloride solution. The solution is dried using sodium sulfate and concentrated under reduced pressure. The residue is digested with methanol, and insoluble material is filtered off. The filtrate is concentrated under reduced pressure, and the residue is purified by column chromatography (SiO2, pentane), giving [(Z)-1,2-difluoro-2-(4-propylcyclohexyl)vinyl]triethylsilane as a colourless oil.

Workup

  1. additionare added at 0° C
  2. temperatureThe mixture is warmed slowly
  3. extractionthe batch is extracted with MTBE
  4. extractionThe aqueous phase is extracted with MTBE
  5. washthe combined organic phases are washed with water and saturated sodium chloride solution
  6. customThe solution is dried
  7. concentrationconcentrated under reduced pressure
  8. filtrationis filtered off
  9. concentrationThe filtrate is concentrated under reduced pressure
  10. customthe residue is purified by column chromatography (SiO2, pentane)

Sources & evidence

ORD record
ord-4c7d1c466dbf4fc9915e6d8b45541f0d
Source dataset
uspto-grants-2015_02
Patent number
US08945420B2

Reaction notes

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