4-Bromoanisole → HCID 10879611, compound

Participants

Reaction Steps

As described by Buchwald et al. (J. Org. Chem. 2002, 106): in a flask was added successively: 187 mg (0.198 mmol) Pd2 dba3, 247 mg (0.791 mmol) 2-(Di-t-butylphosphino)-2′-methybiphenyl, and 1.555 g (4.747 mmol) cesium carbonate. The mixture was put under argon and 740 mg (3.956 mmol) 4-bromoanisole, 15 ml of DME and finally 600 mg (3.956 mmol) of methyl 4-nitrobutyrate were successively added. The mixture was stirred vigorously for 1 minute at room temperature and the flask was placed in a preheated oil bath at 50° C. and stirred at this temperature overnight. The reaction mixture was cooled to room temperature, and a saturated NH4Cl solution and ethyl acetate were added. Aqueous phase was extracted 3 times with ethyl acetate and combined organic phases were washed with brine, and concentrated in vacuo. The crude product was purified with flash column chromatography on silica gel (Eluent: heptane/ethyl acetate 0 to 20%) to provide 897 mg (90%) of the title compound as a orange oil.

Provenance & Evidence