Thiophenol → HCID 20991675, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of thiophenol (5 g, 45 mmol) in DMF (100 mL) is added 3-bromo-2,2-dimethyl-propionic acid (CAS#2843-17-6, 3.98 g, 22 mmol), and potassium fluoride (1.56 g, 27 mmol). The reaction is heated at 120° C. overnight. The reaction is then cooled to room temperature and poured into ice water. A white precipitate is filtered and washed with ice water. The solid is then dissolved in 1M aqueous NaOH and is washed with dichloromethane. The aqueous solution is acidified with 1M HCl and the resulting precipitate is collected to provide 2,2-dimethyl-3-phenylsulfanyl-propionic acid; 1H NMR (400 MHz, CDCl3) δ ppm 1.31 (s, 6 H), 2.72 (br. s., 1 H), 3.19 (s, 2 H), 7.09-7.21 (m, 1 H), 7.21-7.32 (m, 2 H), 7.40 (d, J=7.8 Hz, 2 H).

Provenance & Evidence