Methyl iodide → Methyl 3-methyl-5-nitrobenzoate

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Reaction Steps

Following a general procedure from Applied Organometallic Chemistry 2004, 18, 602-604, a solution of 3-(methoxycarbonyl)-5-nitrophenylboronic acid (900 mg, 4.0 mmol) in tetrahydrofuran (16 mL) was added to a round bottom flask charged with palladium acetate (27 mg, 0.12 mmol), tri-1-napthylphosphine (112 mg, 0.27 mmol), potassium phosphate (1.70 g, 8.00 mmol), and methyl iodide (0.370 mL, 5.9 mmol) under nitrogen atmosphere. Water (0.14 mL, 7.8 mmol) was added and the mixture was stirred overnight at rt. The reaction mixture was diluted with water and extracted with ethyl acetate (3×). The combined organics were washed with water and brine, dried, and concentrated in vacuo. The residue was purified by silica gel chromatography (gradient from 0 to 40% ethyl acetate in hexanes) to give 89A (0.36 g, 46%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.54 (s, 3H) 3.98 (s, 3H) 8.19 (s, 1H) 8.23 (s, 1H) 8.67 (s, 1H).

Provenance & Evidence