2-Bromo-5-nitroanisole → HCID 66858326, compound

Participants

Reaction Conditions

Reaction Steps

Step H (1): 3-Methyl-5-(tributylstannyl)isoxazole (2.4 g, 6.4 mmol, H. Yamanaka et. al Tetrahedron, 1991, 47, 5111) and dichlorobis(triphenylphosphine)palladium (II) (45 mg, 0.0643 mmol) were added to a degassed solution of 1-bromo-2-methoxy-4-nitrobenzene (1.26 g, 5.5 mmol) in dioxane (25 mL). The resulting mixture was heated to reflux (105° C. oil bath temperature) for 24 h. The reaction mixture was cooled to rt and concentrated in vacuo. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified using silica gel column chromatography to afford 5-(2-methoxy-4-nitrophenyl)-3-methylisoxazole (600 mg, 40% yield).

Provenance & Evidence