Iodine → HCID 54120429, compound

HRID 2393673Notes

Reaction equation

HRID 2393673 reaction equation
[Mg].II.Br[C:5]1[CH:13]=[CH:12][C:8]([N:9]([CH3:11])[CH3:10])=[CH:7][CH:6]=1.[CH3:14][O:15][Si:16](OC)([O:19][CH3:20])[O:17][CH3:18]>O1CCCC1>[CH3:10][N:9]([C:8]1[CH:12]=[CH:13][C:5]([Si:16]([O:19][CH3:20])([O:17][CH3:18])[O:15][CH3:14])=[CH:6][CH:7]=1)[CH3:11]

Participants

6

Reactant 4

HCID 807IodineHCID 114654-bromo-N,N-dimethylanilineHCID 12682TetramethoxysilaneHCID 5462224Magnesium

Product 1

HCID 54120429HCID 54120429, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In a 200 ml two-necked flask equipped with a dropping funnel were put 1.01 g (41.5 mmol) of magnesium, 50 ml of tetrahydrofuran (THF), and a small amount of iodine in a nitrogen stream, and a solution of 8.32 g (41.6 mmol) of p-bromo-N,N-dimethylaniline in 50 ml of THF was added thereto dropwise at room temperature over a 40-minute period while stirring. After the addition, the mixture was stirred at room temperature for 75 minutes, and a solution of 6.40 g (42.0 mmol) of tetramethoxysilane in 60 ml of THF was further added thereto, followed by stirring at room temperature overnight. The solvent was removed under reduced pressure, and the residue was suspended in 100 ml of toluene and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound in a yield of 75%.

Workup

  1. customIn a 200 ml two-necked flask equipped with a dropping funnel
  2. additionAfter the addition
  3. stirringthe mixture was stirred at room temperature for 75 minutes
  4. stirringby stirring at room temperature overnight
  5. customThe solvent was removed under reduced pressure
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-430ee7e1e1254f81b554982b5f42347b
Source dataset
uspto-grants-1998_09
Patent number
US05807938

Reaction notes

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