Reaction #1885001

Reaction equation

4-propylphenylboric acid

1-bromo-3-chloro-5-fluorobenzene

sodium carbonate

toluene ethanol water

→

4-propyl-1-(3-chloro-5-fluorophenyl)benzene

Yield 97.7%

Solvents

toluene

Conditions

Workup

1. 1
   Temperaturethe mixture was refluxed for 5 hours
2. 2
   Washwashed with 1N hydrochloric acid and water
3. 3
   DryingThen, the resulting solution was dried over magnesium sulfate
4. 4
   workup.DISTILLATIONdistilled under reduced pressure
5. 5
   Otherto remove the solvent
6. 6
   OtherThe residue was purified by silica-gel column chromatography with heptane as eluent
7. 7
   Otherdried under reduced pressure

Procedure

At first, 25.8 g of 4-propylphenylboric acid (S1-1), 30.0 g of 1-bromo-3-chloro-5-fluorobenzene (S1-2), 2.5 g of tetrakis(triphenylphosphine)palladium, 50.1 g of sodium carbonate and 700 ml of a mixed solvent of toluene/ethanol/water=3/3/1 (volume ratio) were added into a reactor under nitrogen atmosphere, and then the mixture was refluxed for 5 hours. Next, the reaction solution was cooled to room temperature, added with toluene and then washed with 1N hydrochloric acid and water. Then, the resulting solution was dried over magnesium sulfate and then distilled under reduced pressure to remove the solvent. The residue was purified by silica-gel column chromatography with heptane as eluent and then dried under reduced pressure to obtain 34.8 g of 4-propyl-1-(3-chloro-5-fluorophenyl)benzene (S1-3). The yield of the compound (S1-3) from (S1-1) was 97.7%.

Source