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

HRID 2253494Notes

Reaction equation

HRID 2253494 reaction equation
[I-:1].[Na+].CN[C@@H]1CCCC[C@H]1NC.Br[C:14]1[CH:15]=[C:16]([CH3:21])[CH:17]=[C:18]([CH3:20])[CH:19]=1.CCCCCCCCCCCC>C(OCC)(=O)C.[Cu]I>[I:1][C:14]1[CH:15]=[C:16]([CH3:21])[CH:17]=[C:18]([CH3:20])[CH:19]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8182DodecaneHCID 136357Benzene, 1-bromo-3,5-dimethyl-HCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 1409241-Iodo-3,5-dimethylbenzene

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.0504 mmol, 5.0 mol %), sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. trans-N,N′-Dimethyl-1,2-cyclohexanediamine (16 μL, 0.10 mmol, 10 mol %), 5-bromo-m-xylene (136 μL, 1.10 mmol), and solvent (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 23 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-6425fe6b9a6e4ddc9679091dd0a08d17
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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