Reacción #805670

Ecuación de reacción

4-bromo-2-fluoro-1-phenol

4-bromo-1-ethoxy-2-fluorobenzene

1-(bromomethyl)-4-propylcyclohexane

potassium carbonate

→

4-bromo-2-fluoro-1-(4-propylcyclohexyl)benzene

Rendimiento 67.3%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was quenched with 100 mL of water
2. 2
   Extracciónextracted with 60 mL of toluene three times
3. 3
   LavadoCombined organic layers were washed with a 2N sodium hydroxide aqueous solution, water and saturated brine
4. 4
   Secadodried over magnesium sulfate
5. 5
   workup.DISTILLATIONa solvent was distilled off by an evaporator
6. 6
   OtroThe residue was purified by silica gel column chromatography

Procedimiento

Under a nitrogen atmosphere, a mixture of 4-bromo-2-fluoro-1-phenol (52) (10.8 g, 56.58 mmol), 1-(bromomethyl)-4-propylcyclohexane (60) (12.4 g, 56.58 mmol) and potassium carbonate (15.6 g, 112.9 mmol) was agitated at 80° C. for 5 hours in 100 mL of DMF. The reaction mixture was quenched with 100 mL of water, and extracted with 60 mL of toluene three times. Combined organic layers were washed with a 2N sodium hydroxide aqueous solution, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was purified by silica gel column chromatography, and thus 4-bromo-2-fluoro-1-(4-propylcyclohexyl)benzene (61) (11.4 g, yield 61.2%) was obtained.

Fuente