Water → 1-bromo-3-phenyl-2-propanone

To a suspension of CuBr (0.143 g, 0.997 mmol) in 25 mL dry ether was slowly added 1M phenylmagnesium bromide (10 mL, 10 mmol). Epibromohydrin (0.87 mL, 10.5 mmol) was then added dropwise. The reaction mixture was allowed to stir at −78° C. to room temperature overnight, poured into H2O and extracted with ether. The extracts were washed with H2O and brine, dried over Na2SO4, filtered and evaporated in vacuo. The crude alcohol thus obtained was dissolved in acetone (400 mL) and chilled in ice, and to this solution was added dropwise 6 mL of Jones reagent (prepared by dissolution of 2.67 g CrO3 in 2.5 mL H2SO4, followed by dilution with H2O to 10 mL). The reaction mixture was stirred at 0° C. for 15 min and was then evaporated in vacuo. The residue was taken up in ethyl acetate, washed repeatedly with water and once with brine, dried over Na2SO4, filtered and evaporated to afford the ketone product as a brown oil (1.6 g, 75%). 1H NMR (DMSO-d6) δ 7.17-7.35 (m, 5H), 4.45 (s, 2H), 3.94 (s, 2H); MS (DCI+) m/z 230 (M+NH4+).

1. extractionextracted with ether
2. washThe extracts were washed with H2O and brine
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. customevaporated in vacuo
6. customThe crude alcohol thus obtained
7. temperaturechilled in ice
8. stirringThe reaction mixture was stirred at 0° C. for 15 min
9. customwas then evaporated in vacuo
10. washwashed repeatedly with water and once with brine
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. customevaporated

ORD record

ord-bf899221f4fe47c0b99b1dc338c08f08

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504520B2