Methanol → N[2-(Bromoacetyl-phenyl)-1,1-dimethyl-ethyl]-2,2,2-trifluoroacetamide

In a round-bottomed flask, N-(1,1-dimethyl-2-phenyl-ethyl)-2,2,2-trifluoroacetamide (6.90 g, 21.0 mmol) was dissolved in methylene chloride (66 ml) and methanol (33 ml). Tetrabutylammonium tribromide (10.6 g, 22.0 mmol) was added to this solution in one portion, and the mixture was allowed to stir at room temperature overnight. The volatiles were then removed in vacuo to 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 (3×10 ml), and the combined organic extracts were then washed with water and dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude oil was purified by column chromatography (silica gel; 60% methylene chloride/hexanes to 10% ethyl acetate/methylene chloride), and the resulting material (5.18 g) was recrystallized from hexanes to afford 3.14 g (41% yield) of pure product as a fluffy white solid.

1. customThe volatiles were then removed in vacuo to an oil, which
2. extractionextracted with 125 ml of saturated aqueous sodium bicarbonate
3. washthe combined organic extracts were then washed with water
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude oil was purified by column chromatography (silica gel; 60% methylene chloride/hexanes to 10% ethyl acetate/methylene chloride)
8. customthe resulting material (5.18 g) was recrystallized from hexanes

ORD-Eintrag

ord-9b7976b5ab774ad9a591a55bd2fd3c9b

Quelldatensatz

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06706743B2