4-Hydroxybenzaldehyde → HCID 59730014, compound

HRID 130732

Reaction equation

HRID 130732 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 59730014HCID 59730014, compound

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-d284882dfca44239b0836b3ccd0b53d2
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Linked notes

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