Benzyl Alcohol → 1-(Benzyloxy)-3,5-dibromobenzene

Temperature

55 °C

To a solution of benzyl alcohol (10.8 g, 100 mmol) in dry DMF (40 mL), 60% NaH (4.4 g, 110 mmol) was added portionwise and the mixture was stirred at 55° C. for 10 min. Then, 1,3,5-tribromobenzene (22.0 g, 70 mmol) was added slowly to the reaction mixture and the resulting solution was heated at 120° C. for 4 h. After cooling to room temperature, the reaction mixture was poured into a mixture of diethyl ether (500 mL) and water (200 mL) along with intense stirring. The organic layer was separated and washed with water (2×100 mL), 5% HCl (100 mL), saturated NaHCO3 aqueous solution (100 mL) and brine (100 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica using hexanes-acetone (10:0.5) as eluent to afford 18.5 g (77%) of title compound as an yellow oil. 1H NMR (CDCl3, 300 MHz): δ 7.45-7.32 (m, 5H); 7.25 (s, 1H); 7.07 (s, 2H); 5.05 (s, 2H).

1. temperaturethe resulting solution was heated at 120° C. for 4 h
2. temperatureAfter cooling to room temperature
3. customThe organic layer was separated
4. washwashed with water (2×100 mL), 5% HCl (100 mL), saturated NaHCO3 aqueous solution (100 mL) and brine (100 mL)
5. dry with materialThe organic phase was dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by column chromatography on silica

ORD record

ord-ae707605d55540abb26417ffd38b9067

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093253B2