Reaction #48608

Reaction equation

2-(2-fluorophenyl)-ethanol

vinyl acetate

sodium carbonate

→

title compound

Yield 72.2%

1-Fluoro-2-(2-vinyloxyethyl)-benzene

Yield 72.2%

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureCool the reaction mixture to room temperature
2. 2
   FiltrationVacuum filter the resultant slurry
3. 3
   Otherto remove inorganic precipitates
4. 4
   Washwashing the collected solid with hexanes
5. 5
   ConcentrationConcentrate
6. 6
   Otherpurify
7. 7
   Wash(silica gel chromatography, eluting with hexanes)

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%).

Source