Hydrochloric Acid → HCID 11075305, compound

HRID 1743618Notes

Reaction equation

HRID 1743618 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH:6]=[C:7]([C:10]#[N:11])[C:8]#[N:9])=[CH:4][CH:3]=1.[CH:14]([Mg]Br)([CH3:16])[CH3:15].Cl>O1CCCC1.[Cu]I>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([CH:7]([C:8]#[N:9])[C:10]#[N:11])[CH:14]([CH3:16])[CH3:15])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 158474-ChlorobenzylidenemalononitrileHCID 178418365HCID 178418365, compound

Product 1

HCID 11075305HCID 11075305, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Solvent

Procedure

First, 1.02 g of (4-chlorobenzylidene)malononitrile was dissolved in 20 ml of tetrahydrofuran, to which a catalytic amount of copper (I) iodide was added, and while stirring under ice cooling, a solution of isopropyl magnesium bromide in tetrahydrofuran (prepared from 0.34 g of magnesium, 10 ml of tetrahydrofuran, and 1.46 ml of isopropyl bromide) was added dropwise, followed by stirring for 30 minutes under ice cooling. Then, 10% hydrochloric acid was added to the reaction mixture, which became acidic and was extracted with ethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.66 g of (1-(4-chlorophenyl)-2-methylpropyl)malononitrile (the intermediate (3)).

Workup

  1. additionwas added
  2. stirringby stirring for 30 minutes under ice cooling
  3. extractionwas extracted with ethyl ether
  4. washThe organic layer was successively washed with 10% hydrochloric acid
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db3a10f36ae84e938b3109853c3b8a1a
Source dataset
uspto-grants-2006_03
Patent number
US07011838B2

Reaction notes

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