3-(4-Bromophenyl)cyclobutan-1-one → HCID 178521618, compound

To a solution of 3-(4-bromo-phenyl)-cyclobutanone (3 g, 13.3 mmol) (J. Med. Chem., 43:721-735(2000)), in anhydrous ether (100 mL) cooled to −20° C. was dropwise added lithium aluminum hydride (1M in THF, 15 mL). The mixture was then allowed to warm to room temperature and stirred for 4 hours. The reaction was slowly quenched with NaOH (1M, 0.8 mL), H2O (0.8 mL) and NaOH (1M, 0.8 mL) sequentially. After stirring for about 30 minutes, the mixture was filtered through a layer of diatomaceous earth and washed with extra ether (100 mL). The filtrate was evaporated under reduced pressure to provide a colorless oil as the title compound (3.01 g, 100%). 1H NMR (300 MHz, CDCl3) δ 2.0 (m, 2 H), 2.76 (m, 2 H), 2.92 (m, 1 H), 4.28 (m, 1 H), 7.09 (d, J=9 Hz, 2 H), 7.41 (d, J=9 Hz, 2 H); (DCl/NH3) m/z 244(M+NH4)+.

1. customThe reaction was slowly quenched with NaOH (1M, 0.8 mL), H2O (0.8 mL) and NaOH (1M, 0.8 mL) sequentially
2. stirringAfter stirring for about 30 minutes
3. filtrationthe mixture was filtered through a layer of diatomaceous earth
4. washwashed with extra ether (100 mL)
5. customThe filtrate was evaporated under reduced pressure

ORD record

ord-cc0cfc18e22040d5a859c60ffc82ebc5

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07553964B2