Water → (E)-4-((3,5-difluoro-4-((3,3,3-trifluoro-1-propen-1-yl)oxy)phenoxy)difluoromethyl)-4'-propyl-1,1'-bi(cyclohexane)

HRID 589216Notes

Reaction equation

HRID 589216 reaction equation
[F:1][C:2]([F:28])([CH:13]1[CH2:18][CH2:17][CH:16]([CH:19]2[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:20]2)[CH2:15][CH2:14]1)[O:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([OH:11])=[C:6]([F:12])[CH:5]=1.[H-].[Na+].Cl/[CH:32]=[CH:33]/[C:34]([F:37])([F:36])[F:35].O>CN1C(=O)CCC1>[F:12][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([F:10])[C:7]=1[O:11]/[CH:32]=[CH:33]/[C:34]([F:37])([F:36])[F:35])[O:3][C:2]([F:1])([F:28])[CH:13]1[CH2:14][CH2:15][CH:16]([CH:19]2[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:20]2)[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5709018trans-1-Chloro-3,3,3-trifluoropropeneHCID 899589264-(Difluoro(4'-propyl-[1,1'-bi(cyclohexane)]-4-yl)methoxy)-2,6-difluorophenol

Product 1

HCID 90282473(E)-4-((3,5-difluoro-4-((3,3,3-trifluoro-1-propen-1-yl)oxy)phenoxy)difluoromethyl)-4'-propyl-1,1'-bi(cyclohexane)Yield 56%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

4-(Difluoro(4′-propyl-[1,1′-bi(cyclohexane)]-4-yl)methoxy)-2,6-difluorophenol (3.0 g, 7.45 mmol) prepared by known methods and sodium hydride (55%) (0.325 g, 7.45 mmol) were stirred in NMP (N-methylpyroridone) at 60° C. for 30 minutes. (E)-1-Chloro-3,3,3-trifluoro-1-propene (2.43 g, 18.6 mmol) was then added to the reaction solution, and the mixture was stirred at 130° C. for 24 hours. The reaction solution was poured into water, which was extracted with toluene. The combined organic layers were washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled off with an evaporator and the residue was purified by silica gel chromatography and then by recrystallization to give (E)-4-((3,5-difluoro-4-((3,3,3-trifluoro-1-propen-1-yl)oxy)phenoxy)difluoromethyl)-4′-propyl-1,1′-bi(cyclohexane) (56% yield).

Workup

  1. extractionwas extracted with toluene
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off with an evaporator
  5. customthe residue was purified by silica gel chromatography
  6. customby recrystallization

Sources & evidence

ORD record
ord-541dd0efef9940dfa0698403960dcd1d
Source dataset
uspto-grants-2016_01
Patent number
US09228129B2

Reaction notes

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