Sodium Iodide → 1-Iodo-2-(3-methyl-butyl)-benzene

HRID 1436519Notes

Reaction equation

HRID 1436519 reaction equation
[I-:1].[Na+].CN[C@@H]1CCCC[C@H]1NC.Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23]>C(O)CCCC.[Cu](I)I>[I:1][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 210637691-Bromo-2-(3-methyl-butyl)-benzene

Product 1

HCID 541304451-Iodo-2-(3-methyl-butyl)-benzeneYield 84%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 62761-PentanolSolvent2×

Conditions

Temperature
130 °C

Procedure

Charge a pressure tube with sodium iodide (734 mg, 4.9 mmol) and copper iodide (23 mg, 0.12 mmol). Add trans-N,N′-dimethyl-cyclohexane-1,2-diamine (34 mg, 0.24 mmol) dissolved in 0.5 ml of pentanol. Add 1-bromo-2-(3-methyl-butyl)-benzene dissolved in 0.5 ml of pentanol. Purge with nitrogen, cap the tube and heat at 130° C. for 3 days. Load onto a silica gel cartridge eluting with hexane to obtain the title compound as a colorless liquid (587 mg, 84%).

Workup

  1. customPurge with nitrogen
  2. customcap the tube
  3. washLoad onto a silica gel cartridge eluting with hexane

Sources & evidence

ORD record
ord-b0f663f761d04ce4b28496572ba9de5b
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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