Water → HCID 21930372, compound

HRID 1243701Notes

Reaction equation

HRID 1243701 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[O:18])[C:12]=2[OH:19])[CH:3]=1.Br[CH2:21][CH2:22][OH:23].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:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[O:18])[C:12]=2[O:19][CH2:21][CH2:22][OH:23])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 108982-Bromoethanol2×HCID 21930371HCID 21930371, compound

Product 1

HCID 21930372HCID 21930372, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-2-(3-formyl-2-hydroxyphenoxy)benzonitrile (0.30 g, 1.11 mmol), 2-bromoethanol (0.10 mL, 0.18 g, 1.4 mmol) and cesium carbonate (0.43 g, 1.3 mmol) were heated with stirring in dry DMF (3 mL) at 50° C. After 22 h, 2-bromoethanol (0.19 mL, 0.33 g, 2.7 mmol) was added, and stirring continued for an additional 24 h at 50° C. 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 (3×), water (1×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 4-chloro-2-[3-formyl-2-(2-hydroxyethoxy)phenoxy]benzonitrile (0.29 g, 83%) as a tan oil, which was used without further purification.

Workup

  1. waitcontinued for an additional 24 h at 50° C
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ethyl acetate
  4. customThe ethyl acetate layer was separated
  5. washwashed with 1N sodium hydroxide solution (3×), water (1×), brine (1×)
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d60188a5071a46099bd5e16fb84fb929
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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