PYRIDINE, 2,6-DIFLUORO-4-IODO- synthesis
- Product Name:PYRIDINE, 2,6-DIFLUORO-4-IODO-
- CAS Number:685517-71-9
- Molecular formula:C5H2F2IN
- Molecular Weight:240.98
685517-67-3
94 suppliers
$16.00/1g
685517-71-9
113 suppliers
$22.00/250mg
Yield:685517-71-9 74%
Reaction Conditions:
Stage #1:2,6-difluoro-3-iodopyridine with n-butyllithium;diisopropylamine in tetrahydrofuran;hexane at -78; for 12 h;
Stage #2: with water in tetrahydrofuran;hexane at -78 - 20; for 1 h;
Steps:
4.1.2 DFIDP
n-Butyllithium (1.66mL, 4.15mmol, 2.5mol/L in hexane) was added dropwise to a solution of diisopropylamine (1.30mL, 4.15mmol) in THF (2mL) at -78°C. After 25min 2,6-difluoro-3-iodopyridine (1.00g, 4.15mmol) in THF (5mL) was added dropwise into this mixture by cannula. After 12h at -78°C, H2O (0.2mL, 11mmol) in THF (2mL) was added and the mixture was warmed to room temperature during 1h. The mixture was washed with 10% aqueous Na2SO3 (5mL) and extracted with ethyl acetate (3×50mL). The organic extracts were dried (MgSO4) and concentrated in vacuo. Crystallization from hexane afforded the product as colorless crystals (740mg, 74%). 1H NMR (400MHz, CDCl3): δ 7.22 (t, 2H,J=1.2). 13C NMR (100MHz, CDCl3): 161.1 (dd, J=250, 16, 2C), 115.6 (dd, J=24, 10, 2C), 110.3. 19F NMR (376MHz, CDCl3): δ -68.1. GC-MS m/z calcd. for C5H2F2IN [M+]: 241, found: 241. MP: 78-80°C.
References:
Jin, Xin;Cramer, Jacob R.;Chen, Qi-Wei;Liang, Hai-Lin;Shang, Jian;Shao, Xiang;Chen, Wei;Xu, Guo-Qin;Gothelf, Kurt V.;Wu, Kai [Chinese Chemical Letters,2017,vol. 28,# 3,p. 525 - 530]
685517-67-3
94 suppliers
$16.00/1g
685517-71-9
113 suppliers
$22.00/250mg
1513-65-1
338 suppliers
$6.00/5g
1513-65-1
338 suppliers
$6.00/5g
685517-71-9
113 suppliers
$22.00/250mg