p-Bromoacetophenone → 2-(4-Bromophenyl)propan-2-ol

Temperature

-50 °C

1-(4-Bromophenyl)ethanone (9.25 g, 46.5 mmol) was dissolved in tetrahydrofuran (200 mL). The solution was cooled in a −50° C. bath. Methylmagnesium bromide (3M in ether, 46.5 mL, 139 mmol) was added over a 15 min period. The reaction was allowed to warm to room temperature and then stirred for 20 h. The reaction was quenched with saturated ammonium chloride and then extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated to give an oil. The oil was purified on a silica gel column (0-20% ethyl acetate in hexanes) to give the product a colorless oil (9.1 g, 46.2 mmol, 91% yield). MS (ESI) m/z 197.1 [M]+, 199.1 [M+2]+.

1. temperatureto warm to room temperature
2. customThe reaction was quenched with saturated ammonium chloride
3. extractionextracted with ethyl acetate
4. dry with materialThe organic layer was dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customto give an oil
8. customThe oil was purified on a silica gel column (0-20% ethyl acetate in hexanes)

ORD record

ord-86522330519141088ca8b4867b553901

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193692B2