ChemicalBook CAS DataBase List 2-Amino-1-bromonaphthalene

2-Amino-1-bromonaphthalene synthesis

10synthesis methods

Product Name:2-Amino-1-bromonaphthalene
CAS Number:20191-75-7
Molecular formula:C10H8BrN
Molecular Weight:222.08

The crude naphthalen-2-amine HCl salt (790 mg, 5.5 mmol) and TsOH (170 mg, 1.1 mmol) in THF (50 mL) cooled to 0 0C were treated with NBS (982 mg, 5.5 mmol) in THF (30 mL), and the solution was allowed to warm to 23 0C. After stirring for 5 hours, the reaction mixture was washed with saturated aqueous NaHCO3 (30 mL x 2). The organic layer was dried over anhydrous sodium sulfate and was concentrated to afford 2-Amino-1-bromonaphthalene.

93-09-4 Synthesis

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Yield:-

Steps:

Multi-step reaction with 3 steps
1: diphenyl phosphoryl azide; triethylamine / toluene / 24 h / Molecular sieve; Heating / reflux
2: hydrogenchloride / ethyl acetate / 1 h
3: N-Bromosuccinimide; toluene-4-sulfonic acid / tetrahydrofuran / 5 h / 0 - 23 °C

References:

THE SCRIPPS RESEARCH INSTITUTE WO2009/64908, 2009, A1