Cesium fluoride → HCID 66678157, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-bromo-3-(methoxymethyl)benzoate (Intermediate 1, Step 2, 3.00 g, 11.6 mmol), 5-fluoro-2-methylphenylboronic acid (2.67 g, 17.4 mmol), bis(triphenylphosphine)palladium(II) chloride (162 mg, 0.23 mmol) and cesium fluoride (5.28 g, 34.7 mmol) was prepared in dioxane (30 mL) and water (12 mL) under nitrogen atmosphere. The reaction mixture was heated at 90° C. for 3 hours. The reaction mixture was cooled at RT, diluted with MTBE (150 mL) and the layers were separated. The organic layer was washed with brine (50 mL). The aqueous layers were extracted with MTBE (100 mL). The organic layers were combined, dried over MgSO4 and concentrated under reduced pressure. After purification by flash chromatography (silica, EtOAc/heptane), the title compound was obtained as a colorless oil (2.88 g, 86%). HPLC (Method A), Rt 5.0 min (purity: 98.7%). LC/MS (Method B): 288.9 (M+H)+.

Provenance & Evidence