ChemicalBook CAS DataBase List 1-Boc-3-(4-bromophenyl)-3-fluoroazetidine

1-Boc-3-(4-bromophenyl)-3-fluoroazetidine synthesis

5synthesis methods

Product Name:1-Boc-3-(4-bromophenyl)-3-fluoroazetidine
CAS Number:1357614-51-7
Molecular formula:C14H17BrFNO2
Molecular Weight:330.19

1-Boc-3-(4-bromophenyl)-3-hydroxyazetidine

1357614-50-6
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1-Boc-3-(4-bromophenyl)-3-fluoroazetidine

1357614-51-7
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Yield:1357614-51-7 97%

Reaction Conditions:

with (bis-(2-methoxyethyl)amino)sulfur trufluoride in dichloromethane at -78 - 20;

Steps:

5 Preparation 5: tert-butyl-3-(4-bromophenyl)-3-fluoroazetidine-1-carboxylate

Tert-butyl-3-(4-bromophenyl)-3-hydroxyazetidine-1-carboxylate (Preparation 4, 25 g, 0.076 mol) in CH₂Cl₂(500 mL) was cooled to -78° C. To this slurry was slowly added BAST (20.2 g, 0.09 mol) via addition funnel. The temperature of the reaction was increased slowly from -78° C. to ambient temperature. The mixture was stirred at ambient temperature overnight. LC/MS indicated that the reaction was complete. The reaction was quenched with saturated aqueous NaHCO₃solution (500 mL) and 1M NaOH (500 mL). The aqueous layer was extracted with CH₂Cl₂(2×800 mL). The combined organics were washed with aqueous citric acid (2×700 mL), dried over Na₂SO₄, filtered, and concentrated to afford the desired product as tan solid (24.4 g, 97% yield). ¹H NMR (CDCl₃) δ 7.5 (d, 2H), 7.3 (d, 2H), 4.4 (m, 2H), 4.2 (m, 2H), 1.4 (s, 9H).

References:

US2012/35122,2012,A1 Location in patent:Paragraph 0628; 0629

398489-26-4 Synthesis