Methylparaben → Methyl 4-[(2-fluorophenyl)methoxy]benzoate

Temperature

52.5 °C

Methylparaben (8.85 g, 58.19 mmol) and K2CO3 (16.1 g, 116.38 mmol) were stirred in acetonitrile (100 mL) for 5 minutes and then 2-fluorobenzyl bromide (10 g, 52.9 mmol) was added. The suspension was heated to 50-55° C. and held for 2 hours. The mixture was then cooled to 20-25° C., filtered, and the filtrate solution concentrated to a thick residue. The residue was then dissolved in CH2Cl2, washed with a 1 M Na2CO3 solution, dried over Na2SO4, and concentrated to a solid. The solid was then stirred vigorously for 1 hour in just enough hexanes to allow for agitation (˜40 mL) and then cooled to 0-5° C. After 15 minutes, the product was isolated by filtration and washed with ˜25 mL of hexanes. After drying under vacuum, 1 was isolated as a white solid (13.1 g, 87% yield).

1. temperatureThe mixture was then cooled to 20-25° C.
2. filtrationfiltered
3. concentrationthe filtrate solution concentrated to a thick residue
4. dissolutionThe residue was then dissolved in CH2Cl2
5. washwashed with a 1 M Na2CO3 solution
6. dry with materialdried over Na2SO4
7. concentrationconcentrated to a solid
8. temperaturecooled to 0-5° C
9. waitAfter 15 minutes
10. customthe product was isolated by filtration
11. washwashed with ˜25 mL of hexanes
12. customAfter drying under vacuum

ORD record

ord-207e6db56a6040b2af91538a0d839301

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759542B2