Potassium Carbonate → HCID 57565879, compound

HRID 1728240Notes

Reaction equation

HRID 1728240 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11]([O:13][C:14](=[O:19])[C:15](Br)([CH3:17])[CH3:16])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:11]([O:13][C:14](=[O:19])[C:15]([O:10][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:17])[CH3:16])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 27373285-Fluorosalicylaldehyde

Product 1

HCID 57565879HCID 57565879, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

5-Fluoro-2-hydroxy-benzaldehyde (14 g, 100 mmol), 2-bromo-2-methyl-propionic acid ethyl ester (19.5 g, 100 mmol), K2CO3 (27 g, 196 mmol) and KI (0.97 g, 5.8 mmol) were mixed in DMF (150 mL). Then the reaction mixture was heated at 110° C. for 3 h. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with aqueous 1N NaOH. Then the organic layer was separated, dried over Na2SO4 and concentrated to give title compound (9 g).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with aqueous 1N NaOH
  5. customThen the organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1d081ccca9e742b78f1b36fa998821cc
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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