Hydrochloric Acid → HCID 117599786, compound

Temperature

23 °C

Under nitrogen, to 2-fluoro-6-nitrobenzoic acid (1.27 g, 6.28 mmol, 1.00 equiv) in CH2Cl2 (20 mL) at 23° C. was added oxalyl chloride (0.585 mL, 6.91 mmol, 1.10 equiv) and DMF (16 μL, 0.19 mmol, 3.0 mol %). After stirring for 1 hr at 23° C., the reaction mixture was cooled to 0° C. and triethylamine (2.63 mL, 18.8 mmol, 3.00 equiv) and 3-(2,2-difluoroethoxy)aniline (1.09 g, 6.28 mmol, 1.00 equiv) were added. After stirring for 15 min at 0° C., 3N HCl aq (50 mL) was added. The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×3.0 mL). The combined organic phases were washed with brine (3.0 mL) and dried (MgSO4). The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc to afford 1.07 g of the title compound (50% yield).

1. temperaturethe reaction mixture was cooled to 0° C.
2. stirringAfter stirring for 15 min at 0° C.
3. customThe phases were separated
4. extractionthe aqueous phase was extracted with CH2Cl2 (3×3.0 mL)
5. washThe combined organic phases were washed with brine (3.0 mL)
6. dry with materialdried (MgSO4)
7. concentrationThe filtrate was concentrated in vacuo
8. customthe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc

ORD record

ord-2d6011ff52584fc2ba8fe36f53a1022a

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216985B2