Ethanol → Benzeneacetic acid, 4-fluoro-, ethyl ester

Temperature

0 °C

A mixture of 2-(4-fluorophenyl)acetic acid (23.5 g, 152 mmol) in thionyl chloride 56 mL, 762 mmol) was refluxed for 2 hours and then concentrated in vacuo. The residue was diluted with 200 mL DCM, and stirred at 0° C. The mixture was treated with EtOH (9.8 mL, 168 mmol) and TEA (26 mL) dropwise. The mixture was then stirred for 2 hours. The mixture was quenched with 20 mL H2O and extracted with DCM (3×50 mL). The combined organics were washed with H2O (3×50 mL) and brine 20 mL, dried over anhydrous Na2SO4, and concentrated in vacuo to give 24.7 g of a pale yellow oil.

1. temperaturewas refluxed for 2 hours
2. concentrationconcentrated in vacuo
3. additionThe residue was diluted with 200 mL DCM
4. stirringThe mixture was then stirred for 2 hours
5. customThe mixture was quenched with 20 mL H2O
6. extractionextracted with DCM (3×50 mL)
7. washThe combined organics were washed with H2O (3×50 mL) and brine 20 mL
8. dry with materialdried over anhydrous Na2SO4
9. concentrationconcentrated in vacuo

ORD record

ord-a8b60b25d5e84c05aa1bffc40aa59cc8

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07635715B2