Potassium Carbonate → 4-Bromo-2-fluoro-1-(4-propylcyclohexyl)benzene

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.

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

ORD record

ord-a5273f2884544200b4c056813c64543d

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193908B2