Potassium Carbonate → 5-Bromo-3-methoxy-2-(2-trimethylsilanylethoxymethoxy)benzaldehyde

HRID 12293

Reaction equation

HRID 12293 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([O:10][CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2622385-Bromo-2-hydroxy-3-methoxybenzaldehydeHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 860709695-Bromo-3-methoxy-2-(2-trimethylsilanylethoxymethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 g of 5-bromo-2-hydroxy-3-methoxybenzaldehyde, 23.9 g of potassium carbonate and 12.2 g of (2-chloromethoxyethyl)trimethylsilane is suspended in 500 ml of DMF and stirred at room temperature for 48 hours. The DMF is distilled off in vacuo, the residue is dissolved in ethyl acetate, and the resulting solution is extracted with water. It is then dried over magnesium sulphate and filtered, and the solvent is distilled off. The crude product is purified by silica gel chromatography (heptane/ethyl acetate).

Workup

  1. distillationThe DMF is distilled off in vacuo
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. extractionthe resulting solution is extracted with water
  4. dry with materialIt is then dried over magnesium sulphate
  5. filtrationfiltered
  6. distillationthe solvent is distilled off
  7. customThe crude product is purified by silica gel chromatography (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-ec95a085efed4ea4bd8fe4a25e73c26c
Source dataset
uspto-grants-2010_06
Patent number
US07727989B2

Linked notes

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