Pyridine → tert-Butyl 2-(4-bromophenyl)propan-2-ylcarbamate

Participants

Reaction Steps

To a suspension of 2-(4-bromophenyl)-2-methylpropanamide (3 g) in tert-butanol (31 mL) was added [bis(trifluoroacetoxy)iodo]benzene (8 g) portionwise at room temperature. The reaction mixture was stirred at reflux temperature for 30 min Pyridine (3 mL) was added to the mixture. After being stirred at reflux temperature for 1 h, the reaction mixture was concentrated to dryness. The residue was dissolved in benzene and washed with 1 M citric acid aqueous solution (2 times), sodium bicarbonate aqueous solution (5 times) then brine. The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (0-20% ethyl acetate in hexanes) gave the product (3.29 g, 84%). 1HNMR (CDCl3) 400 MHz δ: 7.43 (d, J=8.6 Hz, 2H), 7.27 (d, J=8.6 Hz, 2H), 1.59 (br s, 6H), 1.48-1.05 (m, 9H).

Provenance & Evidence