Iodine → 2,3-Dichloro-5-iodopyridine

HRID 462816

Reaction equation

HRID 462816 reaction equation
C([Li])CCC.[I:6]I.Br[C:9]1[CH:10]=[C:11]([Cl:16])[C:12]([Cl:15])=[N:13][CH:14]=1>C(OCC)C.CCCCCC>[Cl:15][C:12]1[C:11]([Cl:16])=[CH:10][C:9]([I:6])=[CH:14][N:13]=1

Participants

6

Reactant 3

HCID 807IodineHCID 127477605-Bromo-2,3-dichloropyridineHCID 178418339Butyllithium

Product 1

HCID 218928742,3-Dichloro-5-iodopyridine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

In one embodiment of the present invention, 5-bromo-2,3-dichloropyridine is dissolved in ethyl ether and cooled to about -78° C. A slight excess molar quantity of n-butyl lithium, dissolved in hexane, is slowly added to the reaction mixture with mild agitation. After about 0.5 hour of stirring, a slight excess molar quantity of I2, dissolved in ethyl ether, is added to reaction mixture with mild agitation. After about 0.5 hour of stirring, the reaction mixture is allowed to warm to room temperature and the 2,3-dichloro-5-iodopyridine is isolated employing standard separatory and purification techniques.

Workup

  1. additionis slowly added to the reaction mixture with mild agitation
  2. additionis added to reaction mixture with mild agitation
  3. stirringAfter about 0.5 hour of stirring
  4. temperatureto warm to room temperature

Sources & evidence

ORD record
ord-b1b825a7855043d992d3ed1e62d81722
Source dataset
uspto-grants-1985_05
Patent number
US04517368

Linked notes

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