Water → HCID 21930361, compound

HRID 1178481Notes

Reaction equation

HRID 1178481 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:13]([O:20][CH2:21][CH2:22][CH3:23])=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[O:16].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[CH:19]=[CH:18][CH:17]=[C:14]([CH:15]=[O:16])[C:13]=2[O:20][CH2:21][CH2:22][CH3:23])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 936554-Chloro-2-fluorobenzonitrileHCID 21930377HCID 21930377, compound

Product 1

HCID 21930361HCID 21930361, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-2-fluorobenzonitrile (0.35 g, 2.2 mmol), 3-hydroxy-2-propoxybenzaldehyde (0.40 g, 2.2 mmol) and cesium carbonate (0.72 g, 2.2 mmol) were heated with stirring in dry DMF (4 mL) at 50° C. for 19 h. The reaction mixture was cooled, 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-(3-formyl-2-propoxyphenoxy)-benzonitrile (0.69 g, 98%) as a brown oil, which was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-591c0f21c3534c41b26908d91fafaa00
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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