Iodine → 4-Iodo-1-(methyldiisopropyloxysilyl)benzene

HRID 1836929Notes

Reaction equation

HRID 1836929 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Si:8]([CH3:17])([O:13][CH:14]([CH3:16])[CH3:15])[O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[Mg].[I:19]I>C1COCC1>[I:19][C:2]1[CH:7]=[CH:6][C:5]([Si:8]([CH3:17])([O:13][CH:14]([CH3:16])[CH3:15])[O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 807IodineHCID 5462224MagnesiumHCID 120405694-Bromo1-(methyldiisopropyloxysilyl)benzene2×

Product 1

HCID 120405754-Iodo-1-(methyldiisopropyloxysilyl)benzeneYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4-bromo-1-(methyldiisopropyloxysilyl)benzene (13.35 g, 42.1 mmol) in THF (85 ml) was added slowly dropwise at 0° C. to a suspension of magnesium chips (1.53 g, 63.1 mmol) in THF (10 ml). After one hour, the Grignard reagent of 4-bromo-1-(methyldiisopropyloxysilyl)benzene was added dropwise at 0° C. to iodine (13.87 g, 54 mmol) dissolved in 50 ml of dry THF. After stirring during four hours, the solvent was pumped off and the residue was extracted with dry pentane (200 ml) and filtered. The yellow solution was concentrated to afford 4-iodo-1-(methyldiisopropyloxysilyl)benzene as a yellow oil of in 84% yield. 1H NMR (CDCl3, δ, ppm) 7.76 (2H, d); 7.42 (2H, d); 4.21 (2H, heptuplet); 1.23 (12H, t); 0.37 (3H, s).

Workup

  1. extractionthe residue was extracted with dry pentane (200 ml)
  2. filtrationfiltered
  3. concentrationThe yellow solution was concentrated

Sources & evidence

ORD record
ord-4fa1edfa5aff4892a6f8d1fc41fa868c
Source dataset
uspto-grants-2004_08
Patent number
US06780471B2

Reaction notes

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