ChemicalBook CAS DataBase List 5-Bromoquinoline

5-Bromoquinoline synthesis

11synthesis methods

Product Name:5-Bromoquinoline
CAS Number:4964-71-0
Molecular formula:C9H6BrN
Molecular Weight:208.05

5-Bromoquinoline can be prepared by the reaction of quinoline with dichloromethane and NBS.

611-34-7 Synthesis

611-34-7
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4964-71-0
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Yield:4964-71-0 61%

Reaction Conditions:

Stage #1:5-Aminoquinoline with hydrogen bromide;sodium nitrite in water at 0 - 20; for 0.0833333 h;
Stage #2: with hydrogen bromide;copper(I) bromide in water at 20 - 75; for 2 h;
Stage #3: with sodium hydroxide in water

Steps:

7
PREPARATION 7 5-Bromoquinoline Quinolin-5-amine (3.37 g, 23.38 mmol) was dissolved in 9 ml of water and 11 ml of hydrogen bromide (48% in water); the resulting solution was cooled at 0°C. Sodium nitrite (1.94 g, 28.12 mmol) dissolved in 9 ml of water was dropwise added. The resultant solution was stirred at room temperature for 5 minutes. This solution was dropwise added to a solution of copper(I) bromide (4.02 g, 28.02 mmol) in 23 mL of HBr (48% in water) at 75°C. The resulting mixture was stirred at room temperature for 2 h. Then the reaction mixture was basified with sodium hydroxide and extracted twice with ethyl acetate. The organic phase is washed with brine, filtered and dried over sodium sulfate. After filtration and evaporation of the solvent, 2.98 g (61 %) of the final product were obtained. ¹H NMR (CDCl3) δ ppm: 7.44 - 7.63 (m, 2 H) 7.84 (d, J=7.42 Hz, 1 H) 8.10 (d, J=8.24 Hz, 1 H) 8.56 (d, J=8.51 Hz, 1 H) 8.94 (br.s., 1H) HPLC/MS (9 min) retention time 5.68 min. LRMS: m/z 208 (M)/21 0 (M+2)

References:

Almirall, S.A. EP2394998, 2011, A1 Location in patent:Page/Page column 16

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