Cesium carbonate → HCID 21930432, compound

HRID 1243695Notes

Reaction equation

HRID 1243695 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[O:18])[C:12]=2[OH:19])[CH:3]=1.Br[CH2:21][CH2:22][F:23].C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[O:18])[C:12]=2[O:19][CH2:21][CH2:22][F:23])[CH:3]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 129822-Fluoroethyl bromideHCID 14798Sodium HydroxideHCID 21930371HCID 21930371, compound

Product 1

HCID 21930432HCID 21930432, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-2-(3-formyl-2-hydroxyphenoxy)benzonitrile (0.29 g, 1.1 mmol), 1-bromo-2-fluoroethane (0.20 mL, 0.34 g, 2.7 mmol) and cesium carbonate (0.41 g, 1.3 mmol) were heated with stirring in dry DMF (5 mL) at 50° C. for 23 h. The reaction mixture was cooled, poured into 1N sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate layer was separate d, washed with 1N sodium hydroxide solution (3×), water (4×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 4-chloro-2-[2-(2-fluoroethoxy)-3-formylphenoxy]benzonitrile (0.35 g) as a tan solid, which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe ethyl acetate layer was separate d
  4. washwashed with 1N sodium hydroxide solution (3×), water (4×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-888361feae214c119e021b59a01fb594
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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