Boron tribromide → HCID 90418209, compound

Temperature

-78 °C

Into a 8-mL sealed tube (1 atm) purged and maintained with an inert atmosphere of nitrogen, was placed ethyl 3-[2-fluoro-4-methoxy-3-(trifluoromethyl)phenyl]propanoate (200 mg, 0.68 mmol, 1.00 equiv), dichloromethane (1.0 mL). This was followed by the addition of BBr3 (1N in dichloromethane) (1.36 mL, 2.00 equiv) dropwise with stirring at −78° C. The resulting solution was warmed to room temperature and stirred for 2 h at 30° C. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of 5 mL of water. The resulting solution was extracted with 3×10 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by TLC-Plate with petroleum ether/EtOAc=3:1. This resulted in 85 mg (45%) of ethyl 3-[2-fluoro-4-hydroxy-3-(trifluoromethyl)phenyl]propanoate as a light yellow solid. Mass spectrum (ESI, m/z): Calcd. for C12H12F4O3, 279.1 (M−H). found 279.1.

1. customInto a 8-mL sealed tube (1 atm)
2. custompurged
3. temperaturemaintained with an inert atmosphere of nitrogen
4. temperatureThe resulting solution was warmed to room temperature
5. stirringstirred for 2 h at 30° C
6. customThe reaction was then quenched by the addition of 5 mL of water
7. extractionThe resulting solution was extracted with 3×10 mL of dichloromethane
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under vacuum
10. customThe residue was purified by TLC-Plate with petroleum ether/EtOAc=3:1
11. customThis resulted in 85 mg (45%) of ethyl 3-[2-fluoro-4-hydroxy-3-(trifluoromethyl)phenyl]propanoate as a light yellow solid

ORD record

ord-23e13989fd1844b29e0cffe1c6f0476d

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1