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

HRID 1927851Notes

Reaction equation

HRID 1927851 reaction equation
Br[C:2]1[CH2:7][C:6](C)([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)C=CN=1.[I-:19].[Na+].C[NH:22][CH2:23][CH2:24]NC.O1CCOC[CH2:28]1>[Cu]I>[I:19][C:23]1[CH:24]=[C:2]([CH3:28])[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:13]=2)[N:22]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 312751,4-DioxaneHCID 68692423HCID 68692423, compound

Product 1

HCID 574686822-Iodo-4-methyl-6-(4-trifluoromethyl-phenyl)pyridine

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

The title compound was prepared from 2-bromo-4-methyl-4-(4-trifluoromethyl-phenyl)-pyridine (example A.57) (29.0 g, 92 mmol), sodium iodide (27.5 g, 183 mmol), copper(I) iodide (0.874 g, 5 mol %) and N,N′-dimethylethylenediamine (1.3 mL, 10 mol %) in dioxane (150 mL) according to the general procedure Ia to d preparation of iodides. Obtained as a light yellow solid (32.72 g, 98%). MS (ISP) 364.2 [(M+H)+].

Sources & evidence

ORD record
ord-7275df22588243ae941dc586eaac1724
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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