Dimethyl Sulfate → 3-Fluoro-2-methoxybenzaldehyde

Temperature

60 °C

To a suspension of 3-fluoro-2-hydroxybenzaldehyde (5.328 g, 38.02 mmol) and potassium carbonate (7.88 g, 57.03 mmol) in acetone (60 mL) was added dimethyl sulphate (3.96 mL, 41.83 mmol). The resulting suspension was stirred at 60° C. for 2 h before being allowed to cool and then concentrated in vacuo. The residue was dissolved in dichloromethane (100 mL) and water (50 mL). The organic phase was washed with saturated sodium bicarbonate (50 mL) with the resulting organic phase being dried (MgSO4) and the solvent evaporated in vacuo to give a pale yellow oil (6.262 g, 38.02 mmol, 100%). δH (300 MHz, CDCl3) 10.40 (1H, s, CHO), 7.60 (1H, d, Ar), 7.30 (1H), m, Ar), 7.10 (1H, m, Ar), 4.10 (3H, s, OCH3).

1. temperatureto cool
2. concentrationconcentrated in vacuo
3. dissolutionThe residue was dissolved in dichloromethane (100 mL)
4. washThe organic phase was washed with saturated sodium bicarbonate (50 mL) with the resulting organic phase
5. dry with materialbeing dried (MgSO4)
6. customthe solvent evaporated in vacuo

ORD record

ord-dea8fbd647054bb8bf75d4a2a50da8c9

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07037932B2