Phenethyl bromide → HCID 46214970, compound

Participants

Reaction Steps

Preparation of 3-(5-Bromo-2-phenethyloxy-phenoxy)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester. A mixture of 3-(5-bromo-2-hydroxy-phenoxy)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (30 mg. 0.08 mmol), (2-bromoethyl)benzene (29 μL, 0.21 mmol), KI (42 mg, 0.25 mmol) and Cs2CO3 (82 mg, 0.25 mmol) in 3 mL DMF was stirred at rt for 18 h. The reaction mixture was diluted with H2O and extracted with EtOAc (3×). The organic layers were dried and purified by RP HPLC (Agilent) to give the title compound as an oil (22 mg, 58%). MS (ESI): mass calcd. for C23H28BrNO4, 462.4; m/z found, 408.0 [M-56+H]+. 1H NMR (CDCl3): 7.38-7.18 (m, 5H), 7.07 (dd, J=8.6, 2.3 Hz, 1H), 6.76-6.74 (m, 2H), 4.24-4.08 (m, 4H), 3.84 (d, J=9.7 Hz, 2H), 3.11 (t, J=7.1 Hz, 2H), 1.58 (s, 3H), 1.45 (s, 9H).

Provenance & Evidence