Tert-butyl 3-hydroxy-3-(4-(trimethylsilyl)phenyl)azetidine-1-carboxylate (35.45 g, 0.14 mol) was heated with KBr (25 g, 0.21 mol) in a mixed solvent of acetic acid (10 mL) and methanol (100 mL) at 60 °C for 20 min. Subsequently, N-chlorosuccinimide (22.4 g, 0.17 mol) was added to the reaction mixture and stirring was continued at 60 °C for 2 hours. The reaction progress was monitored by LC/MS. After completion of the reaction, the mixture was cooled to room temperature, poured into ice water (1 L) and extracted with chloroform (2 x 800 mL). The organic phases were combined, washed sequentially with 3M NaOH (2 × 600 mL) and water (600 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was washed with ether to afford the target compound tert-butyl 3-(4-bromophenyl)-3-hydroxyazetidine-1-carboxylate (35 g, 76% yield).1H NMR (CDCl3) δ 7.5 (d, 2H), 7.4 (d, 2H), 4.2 (s, 4H), 3.4 (s, 1H), 1.4 (s, 9H).
![1-Azetidinecarboxylic acid, 3-hydroxy-3-[4-(trimethylsilyl)phenyl]-, 1,1-dimethylethyl ester](/CAS/20210305/GIF/1357614-49-3.gif)
