P-Cresol → 4-Methylphenyl 2,4,5-trifluorobenzoate

Temperature

40 °C

The title compound can also be prepared according to the following method: 4-methylphenol (80.0 g, 739.8 mmol) was added to a suspension of 2,4,5-trifluorobenzoic acid (136.8 g, 776.8 mmol) and 1,1-carbonyldiimidazole (83-85% wt, 163.6 g, 849.7 mmol) in EtOAc (1.20 L) at 40° C. The reaction mixture was stirred at 40° C. for 2 hours, then cooled to 20° C. and washed with water (480 mL), a 0.5 M aqueous solution of sodium hydroxide (2×400 mL) and water (400 mL). The organics were concentrated in vacuo and azeotroped with heptane to give a yellow oil. Heptane (640 mL) was added and the mixture was stirred at room temperature for 16 hours. A seed was used to facilitate the formation of a precipitate. The resulting suspension was cooled to 10° C. and filtered. The residue was washed with cold heptane (80 mL) and dried to afford the title compound as an off white solid (147.5 g, 75%):

1. customat 40° C
2. temperaturecooled to 20° C.
3. washwashed with water (480 mL)
4. concentrationThe organics were concentrated in vacuo
5. customazeotroped with heptane
6. customto give a yellow oil
7. stirringthe mixture was stirred at room temperature for 16 hours
8. temperatureThe resulting suspension was cooled to 10° C.
9. filtrationfiltered
10. washThe residue was washed with cold heptane (80 mL)
11. customdried

ORD record

ord-199f4b0a02e848e8a958146640a407b2

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685977B2