Aluminium lithium hydride → 3-(4-Bromophenyl)-3-methylazetidine

Participants

Reaction Steps

To a stirred solution of toluene-4-sulfonic acid 2-(4-bromo-phenyl)-2-cyano-2-methyl-ethyl ester (10 g, 25.38 mmol) in dry tetrahydrofuran (100 mL) was added 1M lithium aluminum hydride (25.3 mL diluted with 25.3 mL of dry tetrahydrofuran) via syringe pump at −10° C. for 1 h and stirring was continued for 30 min at 10° C. The reaction mixture was quenched with water (1 mL), diluted with tetrahydrofuran (3 mL) followed by a 15% aqueous sodium hydroxide solution (1 mL) and water (3 mL), and filtered through a Celite® pad. The filtrate was concentrated in vacuo. Flash chromatography (8% methanol/methylene chloride) afforded 3-(4-bromo-phenyl)-3-methyl-azetidine as an off-white solid (4.0 g, 70%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.52 (s, 3H) 2.42-2.57 (m, 1H) 3.40 (d, J=7.34 Hz, 2H) 3.72 (d, J=7.34 Hz, 2H) 7.15 (d, J=8.80 Hz, 2H) 7.39-7.61 (m, 2H). LC-MS calcd. for C10H12BrN [M+] 226, obsd. 226.0/228.2.

Provenance & Evidence