Cesium carbonate → HCID 67072133, compound

HRID 852404Notes

Reaction equation

HRID 852404 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[F:11])=[O:3].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21].OS([O-])(=O)=O.[K+]>CN(C=O)C>[CH2:23]([O:22][C:20](=[O:21])[C:19]([O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[C:5]([F:11])[CH:6]=1)([CH3:26])[CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 10796Cesium carbonate2×HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester2×HCID 516920Potassium bisulfateHCID 27249122'-Fluoro-4'-hydroxyacetophenone

Product 1

HCID 67072133HCID 67072133, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 12.0 g (77.9 mmol) of 2-fluoro-4-hydroxyacetophenone, 27.9 g (85.6 mmol) of cesium carbonate and 11.6 ml (77.9 mmol) of ethyl 2-bromo-2-methyl-propionate in 200 ml of DMF was heated at 50° C. for 3 days. Twice a day additional 12.7 g (38.9 mmol) of cesium carbonate and 5.8 ml (38.9 mmol) of ethyl 2-bromo-2-methyl-propionate were added (total of 2.5 equivalents). The mixture was neutralized with aqueous 10% KHSO4 and extracted with ether (three times). The organic phases were washed with aqueous 10% KHSO4, aqueous 10% NaCl solution, dried (Na2SO4) and evaporated. The crude product was purified by flash chromatography over silica gel with n-heptane/AcOEt 9:1 to 6:1, to give 16.7 g of the title compound as colorless oil.

Workup

  1. extractionextracted with ether (three times)
  2. washThe organic phases were washed with aqueous 10% KHSO4, aqueous 10% NaCl solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe crude product was purified by flash chromatography over silica gel with n-heptane/AcOEt 9:1 to 6:1

Sources & evidence

ORD record
ord-d1e45f651e0b4cdeb18391ab6cac4a75
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

Loading…