Sodium Hydroxide → HCID 21930422, compound

HRID 1243745Notes

Reaction equation

HRID 1243745 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.[CH2:11]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[OH:22])[CH:17]=[O:18])[CH:12]=[CH2:13].[F-].[K+].[OH-].[Na+]>CN(C=O)C>[CH2:11]([C:14]1[CH:15]=[C:16]([CH:17]=[O:18])[CH:19]=[CH:20][C:21]=1[O:22][C:4]1[CH:3]=[C:2]([Cl:1])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 936554-Chloro-2-fluorobenzonitrileHCID 522689Potassium FluorideHCID 47290143-Allyl-4-hydroxybenzaldehyde

Product 1

HCID 21930422HCID 21930422, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-2-fluorobenzonitrile (0.34 g, 2.2 mmol), 3-allyl-4-hydroxybenzaldehyde (0.34 g, 2.1 mmol) and potassium fluoride (6.37 g, 6.3 mmol) were heated with stirring in dry DMF (4 mL) at 120° C. for 4 h. The reaction mixture was cooled, poured into 0.1N sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate layer was separated, washed with 0.1N sodium hydroxide solution (3×), water (2×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo and the residue purified by chromatography to give 2-(2-allyl-4-formyl-phenoxy)4-chlorobenzonitrile (0.09 g, 15%) as a colourless oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed with 0.1N sodium hydroxide solution (3×), water (2×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo
  8. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-09ba60fa2116457e9ea817206f4025d0
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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