Dimethylformamide → 4-(Benzyloxy)-1-bromo-2-fluorobenzene

To a mixed solution of a commercially available product of 4-bromo-3-fluorophenol (15.0 g, 78.5 mmol) and DMF (30 mL) were added potassium carbonate (21.7 g, 157 mmol) and benzyl bromide (10.2 mL, 86.4 mmol) at room temperature, and the resultant mixture was stirred at room temperature for 20 minutes and then at 70° C. for 40 minutes. The reaction mixture was cooled to room temperature, then water was added to the reaction mixture, and the resultant solution was extracted with ethyl acetate. An organic layer was washed with water and then with saturated brine. An organic layer was dried over anhydrous magnesium sulfate and then filtrated. The solvent was evaporated under a reduced pressure, and the resultant residue was purified by silica gel column chromatography (heptane:ethyl acetate=5:1) to give the title compound (22.7 g, yield: quantitative).

1. extractionthe resultant solution was extracted with ethyl acetate
2. washAn organic layer was washed with water
3. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
4. filtrationfiltrated
5. customThe solvent was evaporated under a reduced pressure
6. customthe resultant residue was purified by silica gel column chromatography (heptane:ethyl acetate=5:1)

ORD record

ord-d385ff52753b4369a063c5f9e2ad8868

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174998B2