ChemicalBook CAS DataBase List 1-(4-AMINO-3-BROMO-PHENYL)-ETHANONE

1-(4-AMINO-3-BROMO-PHENYL)-ETHANONE synthesis

5synthesis methods

Product Name:1-(4-AMINO-3-BROMO-PHENYL)-ETHANONE
CAS Number:56759-32-1
Molecular formula:C8H8BrNO
Molecular Weight:214.06

99-92-3 Synthesis

99-92-3
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56759-32-1
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Yield: 100%

Reaction Conditions:

with N-Bromosuccinimide in acetonitrile at 20; for 20 h;Cooling with ice;

Steps:

23a (23a) 1-(4-amino-3-bromophenyl)ethanone
Example 23 4-acetyl-2-{4-[2-(tetrahydropyran-4-yloxy)ethoxy]phenylamino}benzonitrile (23a) 1-(4-amino-3-bromophenyl)ethanone 1-(4-Aminophenyl)ethanone (10.0 g, 74.0 mmol) was dissolved in acetonitrile (50 mL) and, under ice-cooling, a solution (30 mL) of N-bromosuccinimide (13.8 g, 77.7 mmol) in acetonitrile was added dropwise, and the mixture was stirred at room temperature for 20 hr. The solvent of the reaction mixture was evaporated under reduced pressure, and the obtained residue was dissolved in ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title object compound as a yellow powder (15.8 g, yield 100%). ¹H-NMR (CDCl₃, 400 MHz) δ: 2.49 (3H, s), 4.52-4.70 (2H, br), 6.73 (1H, d, J=8.5 Hz), 7.73 (1H, dd, J=8.5, 1.9 Hz), 8.05 (1H, d, J=1.9 Hz).

References:

Kyoto Pharmaceutical Industries, Ltd.;SHIRAHASE, Hiroaki;TAKAHASHI, Kenji;SHOJI, Yoshimichi;TAKEDA, Shigemitsu US2016/207883, 2016, A1 Location in patent:Paragraph 0644-0646