2-BROMO-6-BROMOQUINOLINE synthesis

6synthesis methods

Product Name:2-BROMO-6-BROMOQUINOLINE
CAS Number:77514-31-9
Molecular formula:C9H5Br2N
Molecular Weight:286.95

6563-11-7 Synthesis

6563-11-7
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77514-31-9
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Yield:77514-31-9 70.5%

Reaction Conditions:

Stage #1: 6-bromoquinoline-N-oxidewith benzoyl chloride;sodium hydroxide in dichloromethane;water at 5;Reflux;
Stage #2: with phosphorus(V) oxybromide in toluene;Schlenk technique;Inert atmosphere;Reflux;

Steps:

Synthesis of 2,6-dibromoquinoline (3)

To a round bottom flask was charged 6-bromoquinoline N-oxide (2) (1.27g, 5.7mmol) and sodium hydroxide (0.44g, 11.0mmol) in water (12.0mL) and CH₂Cl₂ (6.0mL), benzoyl chloride (8.5mmol, 1.0mL) was added slowly to the vigorously stirred mixture [15]. A reflux was observed when the addition was nearly completed. Then the flask was then cooled to 5°C with ice-bath, and addition was resumed. After 1h stirring, the precipitate was filtered off, rinsed well with water (50mL) and CH₂Cl₂ (50mL) respectively, then dried in the air, white product was obtained.

References:

Wang, Danfeng;Liu, Rui;Chen, Chen;Wang, Shifan;Chang, Jin;Wu, Chunhui;Zhu, Hongjun;Waclawik, Eric R. [Dyes and Pigments,2013,vol. 99,# 1,p. 240 - 249]

5332-25-2 Synthesis