Potassium Carbonate → HCID 57565924, compound

HRID 504451Notes

Reaction equation

HRID 504451 reaction equation
[Cl: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]([C:21]1(Br)[CH2:24][CH2:23][CH2:22]1)=[O:20]>CN(C=O)C.COC(C1(Br)CCC1)=O>[CH3:17][O:18][C:19]([C:21]1([O:10][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=2[CH:7]=[O:8])[CH2:24][CH2:23][CH2:22]1)=[O:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 574698Methyl 1-bromocyclobutanecarboxylate

Product 1

HCID 57565924HCID 57565924, compoundYield 104.7%

Reagents, catalysts & solvents 2

HCID 574698Methyl 1-bromocyclobutanecarboxylateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 5-chloro-2-hydroxy-benzaldehyde (10 g, 64 mmol), KI (3 g) and K2CO3 (13 g, 94 mmol) in DMF (100 mL) was added 1-bromo-cyclobutanecarboxylic acid methyl ester (15 g, 77 mmol). The mixture was heated at 140° C. for 1.5 h. Then additional 1-bromo-cyclobutanecarboxylic acid methyl ester (0.5 g, 2.6 mmol) was added and the mixture was heated at 140° C. for additional 10 min, cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was washed with water, dried over anhydrous Na2SO4, concentrated to give the title compound as dark oil (18 g).

Workup

  1. temperaturethe mixture was heated at 140° C. for additional 10 min
  2. temperaturecooled to room temperature
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-30842c7a66e64ece893605f97b87e726
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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