Sodium Iodide → (5-Bromo-2-chlorophenyl)methanamine

Temperature

-20 °C

To a solution of chlorotrimethylsilane (3.55 mL, 27.2 mmol) in acetonitrile (70 mL) was added sodium iodide (3.91 g, 27.2 mmol), and the reaction mixture was stirred at −20° C. for 1 h. Then methyl N-[(5-bromo-2-chlorophenyl)methyl]carbamate (3 g, 7.7 mmol; prepared according to U.S. Pat. No. 6,313,071) was added, and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was then basified with 1 N aqueous sodium hydroxide solution and extracted with ethyl acetate (3×). The organic layers were combined, washed with water and brine and then dried (Na2SO4). The solvent was evaporated to provide the title product (1.4 g).

1. customprepared
2. addition6,313,071) was added
3. stirringthe reaction mixture was stirred at room temperature for 16 h
4. extractionextracted with ethyl acetate (3×)
5. washwashed with water and brine
6. dry with materialdried (Na2SO4)
7. customThe solvent was evaporated

ORD record

ord-15cfe5a0c5d94128a306416440d08e29

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921360B2