ChemicalBook CAS DataBase List 5-BROMO-2-CHLORO-4-(TRIFLUOROMETHYL)PYRIDINE

5-BROMO-2-CHLORO-4-(TRIFLUOROMETHYL)PYRIDINE synthesis

4synthesis methods

Product Name:5-BROMO-2-CHLORO-4-(TRIFLUOROMETHYL)PYRIDINE
CAS Number:823221-93-8
Molecular formula:C6H2BrClF3N
Molecular Weight:260.44

680-15-9 Synthesis

Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate

680-15-9
248 suppliers
$13.00/5g

401892-47-5 Synthesis

401892-47-5
67 suppliers
$17.00/1g

5-BROMO-2-CHLORO-4-(TRIFLUOROMETHYL)PYRIDINE

823221-93-8
98 suppliers
$21.21/250mgs:

Yield: 64%

Reaction Conditions:

with copper(l) iodide in N,N-dimethyl-formamide at 100; for 6 h;

Steps:

13.2 Step 2: 5-Bromo-2-chloro-4-(trijhioromethyl)pyridine
To a stirred solution of 5-bromo-2-chloro-4-iodopyridine (40 g, 126.2 mmol, 1 eq) in DMF (400 mL) was added methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (32.1 mL, 252.5 mmol, 2 eq) followed by CuT (48.2 g, 252.5 mmol, 2 eq). The resulting mixture was heated at 100 °C for 6 h. TLC analysis indicated formation of a non-polar spot. The reaction mixture was diluted with water (200 mL), filtered through a celite pad and washed with n-pentane (2 x 500 mL) and followed by cold water (3 x 1000 mL). Organic layers were separated, dried over Na2SO4 and concentrated under reduced pressure at 30 °C resulted 5-bromo-2-chloro-4-(trifluoromethyl)pyridine (21 g, 64% yield) as a liquid compound. TLC: 5% EtOAc in pet ether; Rf: 0.7

References:

PROPELLON THERAPEUTICS INC.;AL-AWAR, Rima;ISAAC, Methvin;JOSEPH, Babu;LIU, Yong;MAMAI, Ahmed;PODA, Gennady;SUBRAMANIAN, Pandiaraju;UEHLING, David;WILSON, Brian;ZEPEDA-VELAZQUEZ, Carlos Armando WO2019/46944, 2019, A1 Location in patent:Paragraph 00162

81290-20-2 Synthesis