ChemicalBook CAS DataBase List 2-CHLORO-5-NITRO-3-(TRIFLUOROMETHYL)PYRIDINE

2-CHLORO-5-NITRO-3-(TRIFLUOROMETHYL)PYRIDINE synthesis

8synthesis methods

Product Name:2-CHLORO-5-NITRO-3-(TRIFLUOROMETHYL)PYRIDINE
CAS Number:99368-67-9
Molecular formula:C6H2ClF3N2O2
Molecular Weight:226.54

2-HYDROXY-5-NITRO-3-(TRIFLUOROMETHYL)PYRIDINE

99368-66-8
201 suppliers
$5.00/250mg

2-CHLORO-5-NITRO-3-(TRIFLUOROMETHYL)PYRIDINE

99368-67-9
132 suppliers
$7.00/250mg

Yield:99368-67-9 86%

Reaction Conditions:

with thionyl chloride in N,N-dimethyl-formamide at 100; for 10 h;Temperature;

Steps:

8.2 2-Chloro-5-nitro-3-(trifluoromethyl)pyridine
SOCl₂ (18.45 mL, 253 mmol) was added to a solution of 5-nitro-3-(trifluoromethyl)pyridin-2-ol (2.63 g, 12.64 mmol). DMF (1.957 mL, 25.3 mmol) was added and the mixture was at 100° C. for 10 h. Then the solution was concentrated and distributed between EA and saturated NaHCO₃ solution. The combined organic extract was washed with brine, dried over MgSO₄, filtered and concentrated. The resulting 2-chloro-5-nitro-3-(trifluoromethyl)pyridine (2.46 g, 10.86 mmol, 86% yield) was used in the next step without further purification. TLC (PE/EA=5:1, R_f=0.6): ¹H NMR (400 MHz, CDCl₃) δ: 9.23-9.59 (m, 1H), 8.79 (d, J=2.4 Hz, 1H).

References:

GlaxoSmithKline Intellectual Property Development Limited;EIDAM, Hilary Schenck;Raha, Kaushik;Gong, Zhen;Guan, Huiping;Wu, Chengde;Yang, Haiying;Yu, Haiyu;Zhang, Zhiliu;CHEUNG, Mui US2014/275111, 2014, A1 Location in patent:Paragraph 0259; 0260

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680-15-9 Synthesis