Benzyl Chloride → 4-(Benzyloxy)-3-fluorobenzaldehyde

Temperature

40 °C

To a stirring solution of 3-fluoro-4-hydroxybenzaldehyde (508 mg, 3.63 mmol) and CsCO3 (1.25 g, 3.84 mmol) in dry MeCN (5.6 mL) under nitrogen at ambient temperature was added benzyl chloride (0.45 mL, 3.91 mmol) and the mixture heated at 40° C. for 27 h. The mixture was then allowed to cool to rt, was quenched by the addition of aqueous NaOH (2N, 30 mL) and the product extracted with EtOAc (2×50 mL). The combined organic layer was then washed with brine (80 mL) and reduced under vacuum. The residue was then purified by SPE (silica, 10 g cartridge) eluting with cyclohexane:EtOAc (gradient 50:1 to 0:1) to afford the title compound as a colourless solid (623 mg).

1. temperatureto cool to rt
2. customwas quenched by the addition of aqueous NaOH (2N, 30 mL)
3. extractionthe product extracted with EtOAc (2×50 mL)
4. washThe combined organic layer was then washed with brine (80 mL)
5. customThe residue was then purified by SPE (silica, 10 g cartridge)
6. washeluting with cyclohexane

ORD record

ord-649ba0e961304635ba29476963f4843a

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07338960B2