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ChemicalBook CAS DataBase List 5-Bromo-6-chloronicotinic acid
29241-62-1

5-Bromo-6-chloronicotinic acid synthesis

4synthesis methods
-

Yield:29241-62-1 97%

Reaction Conditions:

Stage #1:5-bromo-6-hydroxy-3-pyridinecarboxylic acid with tetramethlyammonium chloride;trichlorophosphate for 3 h;Heating / reflux;
Stage #2: with water at 0; for 2 h;

Steps:

8.B
8B. 5-Bromo-6-chloro-nicotinic acid: To 8A (10 g, 45 mmol) was added tetra-methylammonium chloride (5.4 g, 49 mmol) and phosphorous oxychloride (20 mL) and the reaction was heated at reflux for 3 h. The reaction was poured onto ice and stirred 2 h. The solid was filtered off, dissolved in EtOAc (300 mL) and dried (Na2SO4). After filtration and concentration, 10.5g (97%) of 8B as a pink solid was collected. 1HNMR (400 MHz, DMSO-d6) δ: 8.53 (d, J = 2.02 Hz, 1H) 8.85 (d, J = 2.02 Hz, 1 H) 13.57 (s, 1 H).

References:

BRISTOL-MYERS SQUIBB COMPANY WO2007/70818, 2007, A1 Location in patent:Page/Page column 103

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