1,4-Dibromobenzene → 4-Bromo1-(methyldiisopropyloxysilyl)benzene

HRID 1836928Notes

Reaction equation

HRID 1836928 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.Cl[CH2:11][SiH:12]([O:17][CH:18]([CH3:20])[CH3:19])[O:13][CH:14]([CH3:16])[CH3:15].BrC1C=CC(Br)=CC=1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Si:12]([CH3:11])([O:17][CH:18]([CH3:20])[CH3:19])[O:13][CH:14]([CH3:16])[CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78041,4-DibromobenzeneHCID 123979138ChloromethyldiisopropyloxysilaneHCID 178419617HCID 178419617, compound

Product 1

HCID 120405694-Bromo1-(methyldiisopropyloxysilyl)benzeneYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromophenyl magnesium bromide (7.82 g, 50 mmol) in THF (100 ml) was added at 0° C. to a solution of chloromethyldiisopropyloxysilane (10 g, 48 mmol). The mixture was stirred at room temperature for 24 hours. After evaporation of the solvent, the yellow solid was extracted by 200 ml of dry pentane and filtered. The solvent was then pumped off to afford a yellow oil. Residual 1,4-dibromobenzene was sublimated under vacuum at 80° C. to give 4-bromo-1-(methyldiisopropyloxysilyl)benzene as a colourless oil in 33% yield (5.1 g, 16 mmol). 1H NMR (CDCl3, δ, ppm) 7.52 (4H, m); 4.22 (2H, heptuplet); 1.24 (12H, d); 0.39 (3H, s). 13C NMR (CDCl3, δ, ppm) 136.1, 134.5, 131.3, 125.1, 65.8, 26.1, −2.8. 29Si NMR (CDCl3, δ, ppm) −21.8.

Workup

  1. customAfter evaporation of the solvent
  2. extractionthe yellow solid was extracted by 200 ml of dry pentane
  3. filtrationfiltered
  4. customto afford a yellow oil
  5. customwas sublimated under vacuum at 80° C.

Sources & evidence

ORD record
ord-1f7faa09f72c4f89bf3b147359b0fa55
Source dataset
uspto-grants-2004_08
Patent number
US06780471B2

Reaction notes

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