Bromine → N-(2-Bromophenyl)-2,2,2-trifluoroacetamide

Temperature

25 °C

To a stirred mixture of the N-trifluoroacetylaniline (2.00 mmol) and sodium hydrogen carbonate (0.21 g, 2.50 mmol, 1.25 eq) in methanol (10 mL) at 0° C. is added dropwise bromine (0.113 mL, 2.19 mmol, 1.1 eq). The resulting reaction mixture is then stirred at 25° C. for 30 minutes. The reaction mixture is then evaporated under reduced pressure, and the residue is placed in water made acidic to pH 3 with HCl (10 mL). This aqueous mixture is extracted with ethyl acetate (3×15 mL). The extracts is combined, dried (MgSO4), and evaporated under reduced pressure. The residue is column chromatographed using silica gel (approximately 50 g) and elution with an appropriate solvent system to afford the corresponding 2-bromo-N-trifluoroacetylaniline.

1. customThe resulting reaction mixture
2. customThe reaction mixture is then evaporated under reduced pressure
3. extractionThis aqueous mixture is extracted with ethyl acetate (3×15 mL)
4. dry with materialdried (MgSO4)
5. customevaporated under reduced pressure
6. customchromatographed
7. washsilica gel (approximately 50 g) and elution with an appropriate solvent system

ORD record

ord-95527d8d85d44eebb228c2f45fc656dd

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06465500B1