Methanol → 4-Iodo-1-(methyldimethoxysilyl)benzene

HRID 1836930Notes

Reaction equation

HRID 1836930 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([Si:8]([CH3:17])([O:13][CH:14](C)C)[O:9][CH:10](C)C)=[CH:4][CH:3]=1.CO>C1(C)C=CC(S(O)(=O)=O)=CC=1>[I:1][C:2]1[CH:7]=[CH:6][C:5]([Si:8]([CH3:17])([O:13][CH3:14])[O:9][CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 120405754-Iodo-1-(methyldiisopropyloxysilyl)benzene

Product 1

HCID 120405744-Iodo-1-(methyldimethoxysilyl)benzeneYield 84.5%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

Compound 4-iodo-1-(methyldiisopropyloxysilyl)benzene (11.27 g, 35.5 mmol) was dissolved in dry methanol (12.87 g, 400 mmol). 1% molar of p-toluene sulfonic acid (53 mg, 0.3 mmol) was added all at once. The yellow suspension was stirred for 4 hours. The organic solvent was pumped off and the corresponding crude orange oil was distilled under vacuum (B.p. 59-69° C., 3.10−1 mbar) to afford 4-iodo-1-(methyldimethoxysilyl)benzene as a colourless oil (9 g, 30 mmol) in 82% yield. 1H NMR (CDCl3, δ, ppm) 7.78 (2H, d); 7.37 (2H, d); 3.58 (6H, s); 0.37 (3H, s).

Workup

  1. distillationthe corresponding crude orange oil was distilled under vacuum (B.p. 59-69° C., 3.10−1 mbar)

Sources & evidence

ORD record
ord-b31d4f57a05c442fbc2b9e91b144ec1b
Source dataset
uspto-grants-2004_08
Patent number
US06780471B2

Reaction notes

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