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

HRID 2234138

Reaction equation

HRID 2234138 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+].[CH3:19][Si:20]([CH3:27])([CH3:26])[CH2:21][CH2:22][O:23][CH2:24]Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([O:10][CH2:24][O:23][CH2:22][CH2:21][Si:20]([CH3:27])([CH3:26])[CH3:19])=[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

2 g of 5-Bromo-2-hydroxy-3-methoxy-benzaldehyde is dissolved in 200 ml of DMF and 4.78 g of potassium carbonate and 2.3 g of 2-trimethylsilyl-ethoxymethyl chloride are added. The reaction is stirred at RT for 18 h. The solvents are removed under reduced pressure, the residue is dissolved in ethyl acetate and washed with water. After drying over magnesium sulfate, filtration and evaporation, the product is purified by silica gel chromatography eluting with a gradient of ethyl acetate in heptane. Yield 1.8 g.

Workup

  1. customThe solvents are removed under reduced pressure
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialAfter drying over magnesium sulfate, filtration and evaporation
  5. customthe product is purified by silica gel chromatography
  6. washeluting with a gradient of ethyl acetate in heptane

Sources & evidence

ORD record
ord-35f46b2b9c7c4815a4434cf1b50f9ace
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Linked notes

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