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-de8f676e33fb43c1bc9bd3cc2656ca59

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08907087B2