Potassium Carbonate → 3-(4-Bromo-2-formyl-phenoxy)-2,2-dimethyl-propionic acid methyl ester

HRID 1095165Notes

Reaction equation

HRID 1095165 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C([O-])([O-])=O.[K+].[K+].[CH3:17][O:18][C:19](=[O:35])[C:20]([CH3:34])([CH3:33])[CH2:21]OS(C1C=CC(C)=CC=1)(=O)=O>CN(C=O)C>[CH3:17][O:18][C:19](=[O:35])[C:20]([CH3:34])([CH3:33])[CH2:21][O:10][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 22479327Methyl 3-(p-tolylsulfonyloxy)-2,2-dimethylpropanoate

Product 1

HCID 575659193-(4-Bromo-2-formyl-phenoxy)-2,2-dimethyl-propionic acid methyl esterYield 85.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 5-bromo-2-hydroxy-benzaldehyde (4 g, 20 mmol), KI (1 g) and K2CO3 (4 g, 29 mmol) in DMF (10 mL) was added 2,2-dimethyl-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester (6.9 g, 24 mmol). The mixture was heated at 140° C. for 2 h, and then cooled to room temperature, partitioned between water and ethyl acetate. The organic layer was washed with water (3×), dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to give the title compound (5.4 g).

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with water (3×)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-fba2758d098a4d34b42fece0f2cc4f18
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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