Acetic Acid → HCID 118143095, compound

Temperature

115 °C

In a 40 mL vial was added 2,6-dibromo-3-fluoro-4-trifluoromethoxyaniline (172 mg, 0.489 mmol), followed by tin(II) chloride dihydrate (122 mg, 0.540 mmol, 1.1 eq.). Acetic acid (725 μL) and concentrated hydrochloric acid (580 μL) was added to make a solution. The reaction mixture was heated at 115° C. for 1.5 hours. After cooling the reaction to room temperature, most of acetic acid was removed under vacuum. Water was added and the product was extracted with dichloromethane three times. The organic layer was dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, the crude material was purified using silica gel column chromatography. The recovered 2,6-dibromo-3-fluoro-4-trifluoromethoxyaniline was eluted using a gradient of 5˜10% ethyl acetate in hexanes followed by the desired product, 2-bromo-3-fluoro-4-trifluoromethoxyaniline, which was eluted with 15% ethyl acetate in hexanes (64.8 mg, 0.236 mmol, 48%). 1H NMR (400 MHz, CDCl3) δ 7.06 (dd, J=9.0, 9.0 Hz, 1H), 6.52 (dd, J=9.0, 2.0 Hz, 1H), 4.27 (br, 2H).

1. temperatureAfter cooling
2. customthe reaction to room temperature
3. custommost of acetic acid was removed under vacuum
4. additionWater was added
5. extractionthe product was extracted with dichloromethane three times
6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
7. customAfter removing the solvent under reduced pressure
8. customthe crude material was purified
9. washThe recovered 2,6-dibromo-3-fluoro-4-trifluoromethoxyaniline was eluted

ORD record

ord-d4548f8b83c9446da60e8fb2ec848088

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09340509B2