Sodium Iodide → 2-Iodo-6-methyl-4-(4-trifluoromethyl-phenyl)pyridine

HRID 1989113Notes

Reaction equation

HRID 1989113 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:5]=[C:4]([CH3:18])[N:3]=1.[I-:19].[Na+].CNCCNC>O1CCOCC1.[Cu]I>[I:19][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:5]=[C:4]([CH3:18])[N:3]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 574686462-Bromo-6-methyl-4-(4-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 574686452-Iodo-6-methyl-4-(4-trifluoromethyl-phenyl)pyridine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

Alternatively the title compound was prepared from 2-bromo-6-methyl-4-(4-trifluoromethyl-phenyl)-pyridine (example A.48) (101.0 g, 320 mmol), sodium iodide (91.04 g, 608 mmol), copper(I) iodide (2.89 g, 5 mol %) and N,N′-dimethylethylenediamine (3.31 mL, 11 mol %) in dioxane (304 mL) according to the general procedure Ia to d preparation of iodides. Obtained as a light yellow solid (112.5 g, 100%). MS (ISP) 364.0 [(M+H)+]; mp 91-93° C.

Sources & evidence

ORD record
ord-6b555da158c648cf9c9ffa733c296094
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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