Vinyl Acetate → 1-Fluoro-2-(2-vinyloxyethyl)-benzene

HRID 20330

Reaction equation

HRID 20330 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].[C:11](OC=C)(=O)[CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Ir].[Ir].C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][O:10][CH:11]=[CH2:12]

Participants

6

Reactant 3

HCID 7904Vinyl AcetateHCID 10340Sodium CarbonateHCID 27332962-(2-Fluorophenyl)ethan-1-ol

Product 1

HCID 685635321-Fluoro-2-(2-vinyloxyethyl)-benzeneYield 72.2%

Reagents, catalysts & solvents 2

HCID 6436381Chloro(1,5-cyclooctadiene)iridium(I) dimerCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

Combine 2-(2-fluorophenyl)-ethanol (3.08 g, 22.0 mmol), vinyl acetate (4 mL, 43.3 mmol), anhydrous toluene (22 mL), chloro(1,5-cyclooctadiene)iridium(I) dimer (155 mg, 0.231 mmol), and anhydrous sodium carbonate (1.5 g, 14.2 mmol) in a dry round-bottom flask fitted with a reflux condensor under a nitrogen atmosphere. Heat the resulting mixture to 95° C. for 5 hours. Cool the reaction mixture to room temperature. Vacuum filter the resultant slurry to remove inorganic precipitates, washing the collected solid with hexanes. Concentrate and purify (silica gel chromatography, eluting with hexanes) to give the title compound as a yellow oil (2.64 g, 72%).

Workup

  1. temperatureCool the reaction mixture to room temperature
  2. filtrationVacuum filter the resultant slurry
  3. customto remove inorganic precipitates
  4. washwashing the collected solid with hexanes
  5. concentrationConcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with hexanes)

Sources & evidence

ORD record
ord-7b1b0cb0cdd642c8a96a6098f2f2bb17
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Linked notes

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