Phosphinic Acid → 3,5-Diisopropylbromobenzene

Temperature

-5 °C

To a mixture of 4-bromo-2,6-bis(propan-2-yl)aniline (20.5 g, 80.02 mmol, 1.00 equiv) in 2N hydrochloric acid (210 mL) at −5° C. was added NaNO2 (13.8 g, 200.00 mmol, 2.50 equiv) in portions. The reaction was allowed stir at −5° C. for 10 min. Hypophosphorous acid (90 mL) was then added at −5° C. The reaction was warmed to room temperature and then stirred for 12 h. The resulting solution was extracted with 300 mL of ethyl acetate. The organic layer was concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:100) to give 12 g (62%) of 1-bromo-3,5-bis(propan-2-yl)benzene as a light brown oil. 1H NMR (300 MHz, CDCl3): δ 7.18 (s, 2H), 6.98 (s, 1H), 2.89-2.80 (m, 2H), 1.23 (d, J=6.9 Hz, 12H) ppm.

1. temperatureThe reaction was warmed to room temperature
2. stirringstirred for 12 h
3. extractionThe resulting solution was extracted with 300 mL of ethyl acetate
4. concentrationThe organic layer was concentrated under vacuum
5. customThe residue was purified on a silica gel column
6. washeluted with ethyl acetate/petroleum ether (1:100)

ORD record

ord-7bddca29c0354435b027b8b63dedfcbe

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346761B2