4-Hydroxybenzaldehyde → 2-Chloro-4-(4-formylphenoxy)benzonitrile

HRID 228188Notes

Reaction equation

HRID 228188 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:18]=[C:17](F)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:10][C:11]1[CH:18]=[C:17]([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 1090002-Chloro-4-fluorobenzonitrile

Product 1

HCID 597300142-Chloro-4-(4-formylphenoxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxy benzaldehyde (1 equiv), 2-chloro-4-fluorobenzonitrile (1 equiv) and K2CO3 (2.5 equiv) in anhydrous DMF (0.2 M) were heated at 110° C. under nitrogen during 1 hour (the reaction can be monitored by tlc). After cooling down to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate (3×50 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum (toluene was added to aid DMF evaporation). The crude mixture was purified by flash chromatography using hexanes/ethyl acetate (4:1) as eluent.

Workup

  1. customthe reaction
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum (toluene was added to aid DMF evaporation)
  6. customThe crude mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-f6ea09b088bb4ca49e26313737c6f6b1
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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