Hydrochloric Acid → [4-(5-Methylisoxazol-4-yl)phenyl]acetic acid

Participants

Reaction Steps

To a solution of 0.50 g (1.91 mmol) 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaboro-lan-2-yl)phenylacetic acid in 1.90 ml CH3CN and 1.90 ml water was added 0.48 g (2.29 mmol) 4-iodo-5-methyl-isoxazole, 0.08 g (0.12 mmol) TXPTS, 0.01 g (0.05 mmol) Palladium (II) acetate, and 0.54 mL (3.82 mmol) diisopropylamine. After 20 min in the microwave at 120° C., the reaction mixture was cooled, acidified to a pH of 1 with 1N HCl, extracted with CH2Cl2, and washed with brine. The organic layer was dried over NaSO4, filtered and concentrated in vacuo and afforded 0.57 g of ([4-(5-methylisoxazol-4-yl)phenyl]acetic acid that was used without further purification. 1H NMR (CDCl3, 400 MHz) 7.50-7.47 (m, 2H); 7.39-7.33 (m, 3H); 7.32-7.26 (m, 1H); 3.70 (s, 2H). Electrospray mass spec M+H=218.1.

Provenance & Evidence