Sodium Iodide → 1-Iodo-3,5-dimethylbenzene

HRID 2253495Notes

Reaction equation

HRID 2253495 reaction equation
[I-:1].[Na+].CNCCNC.Br[C:10]1[CH:11]=[C:12]([CH3:17])[CH:13]=[C:14]([CH3:16])[CH:15]=1.CCCCCCCCCCCC>C(OCC)(=O)C.[Cu]I.C1(C)C=CC=CC=1>[I:1][C:10]1[CH:11]=[C:12]([CH3:17])[CH:13]=[C:14]([CH3:16])[CH:15]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 8182DodecaneHCID 136357Benzene, 1-bromo-3,5-dimethyl-

Product 1

HCID 1409241-Iodo-3,5-dimethylbenzene

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
110 °C

Procedure

A Schlenk tube was charged with CuI, sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. N,N′-Dimethylethylenediamine, 5-bromo-m-xylene (136 μL, 1.00 mmol), and toluene (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 110° C. for 22 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL, sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature

Sources & evidence

ORD record
ord-0e6e9380234843d29f14d7f6678a3d42
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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