Water → 4-Chloro-2-(4-formylnaphthalen-1-yloxy)benzonitrile

HRID 1178487Notes

Reaction equation

HRID 1178487 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.[OH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH:22]=[O:23])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH:22]=[O:23])=[CH:14][CH:13]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 936554-Chloro-2-fluorobenzonitrileHCID 3442904-Hydroxy-1-naphthaldehyde

Product 1

HCID 219303864-Chloro-2-(4-formylnaphthalen-1-yloxy)benzonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-2-fluorobenzonitrile (0.31 g, 2.0 mmol), 4-hydroxy-1-naphthaldehyde (0.34 g, 2.0 mmol) and cesium carbonate (0.64 g, 2.0 mmol) were heated with stirring in dry DMF (4 mL) at ambient temperature for 10 days. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was separated, washed with 1N sodium hydroxide solution (2×), water (1×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 4-chloro-2-(4-formylnaphthalen-1-yloxy)benzonitrile (0.34 g, 56%) as a tan solid, which was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-e0902e118a9b4336a97445c550a48365
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

Loading…