Methanol → N-[2-(4-Bromoacetyl-phenyl)-ethyl]-acetamide

In a round-bottomed flask, N-[2-(4-acetyl-phenyl)-ethyl]-acetamide (7.23 g, 35.2 mmol) was dissolved in methylene chloride (120 ml), and methanol (60 ml). Tetrabutylammonium tribromide (17.0 g, 35.2 mmol) was added to this solution in one portion, and the mixture was allowed to stir overnight at room temperature. The volatiles were then removed in vacuo to afford an oil, which was then resuspended in 100 ml of methylene chloride and extracted with 125 ml of saturated aqueous sodium bicarbonate. The aqueous extracts were reextracted with methylene chloride (3×100 ml), and the combined organic extracts were then washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude oil was purified by column chromatography (silica gel; methylene chloride to 7% methanol/methylene chloride), and the resulting material was washed with 110 ml of water to afford 8.27 g (83% yield) of pure product as a white solid. LRMS ([M−1 ]−)=283.0, 284.9.

1. customThe volatiles were then removed in vacuo
2. customto afford an oil, which
3. extractionextracted with 125 ml of saturated aqueous sodium bicarbonate
4. washthe combined organic extracts were then washed with water
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude oil was purified by column chromatography (silica gel; methylene chloride to 7% methanol/methylene chloride)
9. washthe resulting material was washed with 110 ml of water

ORDレコード

ord-5b0af00a054b4c3cbc0168762c8e172e

出典データセット

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06566377B2