Water → HCID 67515312, compound

Temperature

100 °C

To a solution 3-(3-bromo-4-methylphenyl)-5,5-dimethyl-4,5-dihydroisoxazol-4-ol (1.80 g, 6.42 mmol) in glacial acetic acid (70 mL), chromium trioxide (640 mg, 6.42 mmol, 1.0 eq), water (4 mL) and concentrated sulfuric acid (0.8 mL) were successively added and the resulting mixture was stirred at 100° C. for 30 min. The reaction was cooled to room temperature and poured into water (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with water (10 mL), brine (10 mL) dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum. The crude product was purified by flash column chromatography (silica gel, 2% ethyl acetate in hexane) to afford the 800 mg of the desired product as a white solid. 1HNMR (400 MHz, CDCl3) δ 8.29 (d, J=1.0 Hz, 1H), 7.94 (dd, J=1.0, 8.0 Hz, 1H), 7.31 (d, J=8.0 Hz, 1H), 2.44 (s, 3H), 1.46 (s. 3H), 1.24 (s, 3H); ESI-MS (m/z) 282, 284 [(MH)+, Br79,81].

1. temperatureThe reaction was cooled to room temperature
2. extractionextracted with ethyl acetate (3×20 mL)
3. washThe combined organic layers were washed with water (10 mL), brine (10 mL)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under vacuum
7. customThe crude product was purified by flash column chromatography (silica gel, 2% ethyl acetate in hexane)

ORD record

ord-0ebbe2ccc27447e0b7ac93103c6621ab

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169242B2