Acetone → 2-(4-Bromo-2-methoxyphenyl)propan-2-ol

Temperature

-78 °C

To a solution of 5-bromo-2-iodoanisole (668 mg, 2.14 mmol) and acetone (0.471 mL, 6.40 mmol) in tetrahydrofuran (7.62 mL) at −78° C. was added n-BuLi (2.5M in hexane, 0.940 mL, 2.35 mmol) in a dropwise manner. The reaction mixture was stirred at −78° C. for 2 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride, warmed to room temperature and extracted with ethyl acetate (2×). The combined organic layers were dried over magnesium sulfate and filtered, and concentrated under reduced pressure yielding 680 mg of crude oil. Purification by column chromatography (0-10% ethyl acetate/heptanes) afforded the title compound (133 mg, 25% yield) as a clear, colorless oil. MS (ES+) 226.9 (M−H2O+H)+. 1H NMR (400 MHz, CDCl3) δ: 7.20 (d, 1H), 7.06-7.10 (m, 1H), 7.04 (d, 1H), 3.91 (s, 3H), 1.58 (s, 6H).

1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride
2. temperaturewarmed to room temperature
3. extractionextracted with ethyl acetate (2×)
4. dry with materialThe combined organic layers were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customyielding 680 mg of crude oil
8. customPurification by column chromatography (0-10% ethyl acetate/heptanes)

ORD record

ord-e58c053165154d4caa095b5cc1dc77a2

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394285B2