4-Hydroxybenzaldehyde → 3-Chloro-4-(4-formylphenoxy)benzonitrile

HRID 130952

Reaction equation

HRID 130952 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:12]=[C:13]([CH:16]=[CH:17][C:18]=1F)[C:14]#[N:15].C(=O)([O-])[O-].[Cs+].[Cs+].CC(N(C)C)=O>O>[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[C:14]#[N:15]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 1455253-Chloro-4-fluorobenzonitrile

Product 1

HCID 568514253-Chloro-4-(4-formylphenoxy)benzonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Mix 4-hydroxy-benzaldehyde (0.86 g, 7.07 mmol), 3-chloro-4-fluoro-benzonitrile (1.00 g, 6.43 mmol), cesium carbonate (3.14 g, 9.64 mmol) and dimethylacetamide (30 mL) in a flask. Heat to 100° C. for 4 hrs. Let cool to room temperature (rt) and pour into water (200 mL). After trituration, filter the solid formed and dry on a vacuum pump to obtain the product (1.57 g, 95%). 1H NMR (DMSO-d6) 9.96 (s, 1H), 8.29 (d, J=1.8 Hz, 1H), 7.97 (d, J=8.6 Hz, 2H), 7.89 (dd, J=1.8 Hz, 8.6 Hz, 1H), 7.35 (d, J=8.6 Hz, 1H), 7.23 (d, J=8.6 Hz, 2H).

Workup

  1. temperatureLet cool to room temperature (rt)
  2. filtrationAfter trituration, filter the solid
  3. customformed
  4. customdry on a vacuum pump

Sources & evidence

ORD record
ord-c6d3829e73514b4bb3288cb8de2dad08
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Linked notes

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