Iodine → HCID 58909282, compound

HRID 1296112Notes

Reaction equation

HRID 1296112 reaction equation
[Mg].II.BrC(Br)C.[CH:8]([C:11]1[CH:12]=[C:13](Br)[CH:14]=[CH:15][CH:16]=1)([CH3:10])[CH3:9].[C:18]1(=[O:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>O1CCCC1>[CH:8]([C:11]1[CH:12]=[C:13]([C:18]2([OH:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:14]=[CH:15][CH:16]=1)([CH3:10])[CH3:9]

Participants

7

Reactant 5

HCID 807IodineHCID 7967CyclohexanoneHCID 112011,1-DibromoethaneHCID 1384991-Bromo-3-isopropylbenzeneHCID 5462224Magnesium

Product 1

HCID 58909282HCID 58909282, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
70 °C

Procedure

To 1.2 g (50 mmol) of magnesium turnings in 15 mL of dry THF is added a small crystal of iodine followed by 40 μL of dibromoethane. This mixture is placed in a water bath at 50° C. and 3-isopropylbromobenzene (5.0 g, 25 mmol) in 15 mL of dry tetrahydrofuran (THF) is added dropwise over 20 min, while the bath temperature is raised to 70° C. The mixture is stirred and refluxed for 40 additional min. The solution is cooled in an ice-water bath and cyclohexanone (2.0 mL, 19 mmol) in 10 mL of dry THF is added dropwise over 15 min. The ice bath is removed and the mixture is allowed to warm to ambient temperature over 1 h. The solution is decanted into aqueous saturated NH4Cl, and combined with an ether wash of the residual magnesium turnings. The organic phase is washed twice more with aqueous NH4Cl, dried over anhydrous Na2SO4, filtered and concentrated. Chromatography on silica gel, eluting with 10% ethyl acetate in heptane, affords 2.7 g (12 mmol, 60%) of compound 1 as an oil: 1H NMR (CDCl3) δ 7.39 (m, 1H), 7.3 (m, 2H), 7.12 (m, 1H), 2.92 (m, 1H), 1.84–1.54 (m, 10H), 1.26 (d, J=7 Hz, 6H).

Workup

  1. customThis mixture is placed in a water bath at 50° C.
  2. temperaturerefluxed for 40 additional min
  3. temperatureThe solution is cooled in an ice-water bath
  4. customThe ice bath is removed
  5. temperatureto warm to ambient temperature over 1 h
  6. customThe solution is decanted into aqueous saturated NH4Cl
  7. washwash of the residual magnesium turnings
  8. washThe organic phase is washed twice more with aqueous NH4Cl
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. washChromatography on silica gel, eluting with 10% ethyl acetate in heptane

Sources & evidence

ORD record
ord-330a2d1115b14ea6aea1bed35b36aafe
Source dataset
uspto-grants-2007_07
Patent number
US07244725B2

Reaction notes

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