ChemicalBook CAS DataBase List 4-CHLORO-3-IODOPYRIDINE

4-CHLORO-3-IODOPYRIDINE synthesis

6synthesis methods

Product Name:4-CHLORO-3-IODOPYRIDINE
CAS Number:89167-34-0
Molecular formula:C5H3ClIN
Molecular Weight:239.44

626-61-9

89167-34-0

The general procedure for the synthesis of 4-chloro-3-iodopyridine from 4-chloropyridine was as follows: suspension of 4-chloropyridine (10 g, 0.067 mol) in dry THF (150 mL) and slow dropwise addition of LDA (134 mL, 1 M hexane solution) at a temperature below -70 °C. The reaction mixture was stirred at -78 °C for 30 min before adding an anhydrous THF solution of I2 (17 g, 0.067 mol), keeping the internal temperature below -65 °C for 10 min. Subsequently, the reaction mixture was slowly warmed up to room temperature over a period of 2 hours and stirring was continued at room temperature for 30 minutes. Upon completion of the reaction, the mixture was poured into 20% aqueous Na2SO3 solution (100 mL) and extracted with EtOAc (100 mL, three times). The organic layer was washed sequentially with aqueous NaHCO3 (50 mL) and saturated aqueous NaCl (50 mL), dried and the solvent was evaporated. The product was purified by washing with petroleum ether (20 mL) to give 4-chloro-3-iodopyridine (6.2 g, 38% yield).'' HNMR (400 MHz, MeOD) δ 8.92 (s, 1H), 8.43-8.41 (d, 1H, J = 8Hz), 7.62-7.60 (d, 1H, J = 8Hz).

89282-03-1
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$45.00/50mg

89167-34-0
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$10.00/250mg

Yield: 58%

Reaction Conditions:

Stage #1:3-iodo-pyridin-4-ol with trichlorophosphate for 4 h;Heating / reflux;
Stage #2: with ammonia;water at 0 - 20;

Steps:

56.2
Step 2. 4-chloro-3-iodopyridine (47)[00371] A stirred solution under nitrogen of 46 (2.00 g, 9.05 mmol) in POCl₃ (20 ml) was heated to reflux for four hours, then rt. The reaction mixture was poured slowly into ice and the pH was adjusted to 10-1 1 with an aqueous solution of ammonium hydroxide. The aqueous layer was extracted twice with dichloromethane.The combined organic layer was washed with brine, dried over anhydrous Na₂SC^, filtered and concentrated to afford the title compound 47 (1.27 g, 5.30 mmol, 58%) as a brown solid. MS: 239.9 (M+l).

References:

METHYLGENE, INC.;RAEPPEL, Stephane;SAAVEDRA, Oscar;CLARIDGE, Stephen;VAISBURG, Arkadii;GAUDETTE, Frederic;ISAKOVIC, Ljubomir;DEZIEL, Robert WO2008/46216, 2008, A1 Location in patent:Page/Page column 170

626-61-9 Synthesis

626-61-9
57 suppliers
$365.00/500mg

89167-34-0
117 suppliers
$10.00/250mg

References

7379-35-3 Synthesis