Dimethyl Sulfate → 2-Bromo-5-fluoroanisole

Temperature

60 °C

To a suspension of 2-bromo-5-fluorophenol (20.0 g, 104.7 mmol) and potassium carbonate (21.71 g, 157.1 mmol) in acetone (200 mL) was added dimethyl sulphate (10.90 mL, 115.2 mmol). The resulting suspension was allowed to stir at 60° C. for 2 h before being allowed to cool and then concentrated in vacuo. The residue was dissolved in ether (200 mL) and water (100 mL). The organic phase was washed with aqueous hydrochloric acid (2 N, 50 mL), saturated sodium bicarbonate solution (50 mL) with the resulting organic phase being dried (MgSO4) and the solvent evaporated in vacuo to give a pale yellow oil (21.46 g, 100%). δH (300 MHz, CDCl3) 7.45 (1H, dd, Ar), 6.70-6.55 (2H, m, Ar), 3.90 (3H, s, OCH3).

1. temperatureto cool
2. concentrationconcentrated in vacuo
3. dissolutionThe residue was dissolved in ether (200 mL)
4. washThe organic phase was washed with aqueous hydrochloric acid (2 N, 50 mL), saturated sodium bicarbonate solution (50 mL) with the resulting organic phase
5. dry with materialbeing dried (MgSO4)
6. customthe solvent evaporated in vacuo

ORD record

ord-439f8454dc544764986cb139c3c6220d

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07417064B2