Potassium Carbonate → HCID 57743363, compound

HRID 1095171Notes

Reaction equation

HRID 1095171 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]([C:19]1([CH2:23]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:22][O:21][CH2:20]1)[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:23][C:19]2([CH2:17][CH3:18])[CH2:22][O:21][CH2:20]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 11425703(3-Ethyloxetan-3-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 57743363HCID 57743363, compoundYield 47.8%

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 toluene-4-sulfonic acid 3-ethyl-oxetan-3-ylmethyl ester (19 g, 70 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 for 3 times, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to give the title compound (10 g).

Workup

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

Sources & evidence

ORD record
ord-49df06bc6d5846ab81d7002d5fec2e82
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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