Sodium Carbonate → HCID 85941970, compound

Participants

Reaction Conditions

Reaction Steps

2,4-Dichloro-5-fluoropyrimidine (0.50 g, 3.0 mmol) and 4-carboxyphenyl boronic acid (0.5 g, 3.0 mmol) were dissolved in dimethoxyethane (20 mL) in a screw cap test tube and 6 mL 2M Na2CO3 was added followed by 80 mg (0.069 mmol) tetrakis(triphenylphosphine)palladium. Argon was bubbled through the reaction mixture for 5 minutes and then the reaction mixture was heated to 85° C. overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to a solid, which was purified by chromatography on silica (MeOH 5%/CH2Cl2) to give 0.22 g (0.87 mmol, 29% yield) of 4-(2-chloro-5-fluoropyrimidin-4-yl)-benzoic acid as a white solid. 1H NMR 500 MHz (MeOH-d4): 8.85 (m, 1H), 8.20 (m, 4H).

Provenance & Evidence