Acetic Acid → HCID 67814794, compound

Temperature

110 °C

To a solution of (3-methylisoxazol-5-yl)methyl acetate (0.979 g, 6.31 mmol) in AcOH (10 mL, 175 mmol) was added N-bromosuccinimide (1.30 g, 7.30 mmol) and H2SO4 (0.65 mL, 12.19 mmol). The reaction was heated to 110° C. After 1 h, the reaction mixture was cooled to room temperature and carefully poured into a beaker containing ice and saturated NaHCO3. The bi-phasic was vigorously stirred and basic solution (pH˜8-9) was extracted with EtOAc (2×15 mL). The organic layer was washed with 2% sodium thiosulfate, washed with brine (20 mL), dried over Na2SO4, and concentrated to give a light yellow oil. The oil was purified on Biotage system (isocratic elution 10% EtOAc:90% Hexanes) to give the titled compound (1.30 g, 5.55 mmol, 88% Yield) as a colorless yellow oil. LC/MS: m/z 234 [M+H]+.

1. temperaturethe reaction mixture was cooled to room temperature
2. additioncarefully poured into a beaker
3. extractionbasic solution (pH˜8-9) was extracted with EtOAc (2×15 mL)
4. washThe organic layer was washed with 2% sodium thiosulfate
5. washwashed with brine (20 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customto give a light yellow oil
9. customThe oil was purified on Biotage system (isocratic elution 10% EtOAc:90% Hexanes)

ORD record

ord-b4de2aa1eab2446ab688e8d74876bd8f

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249161B2