Benzyl Bromide → N-(2-benzyloxy-4-nitro-phenyl)-acetamide

Participants

Reaction Steps

N-(2-Hydroxy-4-nitro-phenyl)-acetamide (417) (17 g, 86.7 mmol) was dissolved in a mixture of acetone (200 mL) and THF (200 mL). Potassium-carbonate (24 g, 173.4 mmol, 2 equiv.) was added as a dry powder and the solution turned deep red. Benzyl-bromide (16.3 g, 95.37 mmol, 1.1 equiv.) was added and the mixture stirred at room temperature for 20 h. TLC (Rf: 0.5 compared to Rf: 0.2–0.3 for compound 417 in 1:1 hexane/EtOAc) indicated complete alkylation at this point. The mixture was poured into ice water (˜1000 mL) and a precipitate formed while stirring for 20 min. The precipitate was collected by filtration under reduced pressure, washed with water (3×100 mL) and dried under high vacuum for 16 h to give the desired product (418) as a faintly yellow powder (13 g, 45.4 mmol, 51.7% yield). LC-MS was inconclusive. The product was used in the next step without further characterization

Provenance & Evidence