Potassium Carbonate → HCID 57566223, compound

HRID 1095159Notes

Reaction equation

HRID 1095159 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+].[CH2:17]([O:19][C:20](=[O:25])[C:21](Br)([CH3:23])[CH3:22])[CH3:18]>CN(C=O)C>[CH2:17]([O:19][C:20](=[O:25])[C:21]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:23])[CH3:22])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 728635-Bromosalicylaldehyde

Product 1

HCID 57566223HCID 57566223, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 5-bromo-2-hydroxy-benzaldehyde (14 g, 70 mmol), KI (5 g) and K2CO3 (19 g, 140 mmol) in DMF (100 mL) was added 2-bromo-2-methyl-propionic acid ethyl ester (17.6 g, 90 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, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to give the title compound (15 g).

Workup

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

Sources & evidence

ORD record
ord-9b31793bcb5f43e7bfeed1b2aa7dd159
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

Loading…