Water → HCID 86636411, compound

HRID 1255611Notes

Reaction equation

HRID 1255611 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10](F)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])#[N:2].[Br:14][C:15]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:16]=1[CH:17]=[O:18].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:14][C:15]1[CH:22]=[CH:21][C:20]([O:23][C:10]2[CH:11]=[CH:12][C:3]([C:1]#[N:2])=[C:4]([CH:9]=2)[C:5]([O:7][CH3:8])=[O:6])=[CH:19][C:16]=1[CH:17]=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 3871792-Bromo-5-hydroxybenzaldehydeHCID 11984295METHYL 2-CYANO-5-FLUOROBENZOATE

Product 1

HCID 86636411HCID 86636411, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-cyano-5-fluorobenzoate (4.48 g, 25.0 mmol), 2-bromo-5-hydroxybenzaldehyde (5.03 g, 25.0 mmol), and potassium carbonate (4.14 g, 30.0 mmol) in N,N-dimethylformamide (50 mL) was stirred at 80° C. overnight. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (chloroform) to give methyl 5-(4-bromo-3-formylphenoxy)-2-cyanobenzoate (5.35 g, 71%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel chromatography (chloroform)

Sources & evidence

ORD record
ord-657ac28275a54ce19c6138130e1f1ddf
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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