Acetic Acid → HCID 13347277, compound

HRID 1098762Notes

Reaction equation

HRID 1098762 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10]C(C#N)=[C:6]([Br:12])[CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].[CH3:15][C:16]([OH:18])=[O:17]>O.OS(O)(=O)=O>[C:1]([C:4]1[CH:11]=[CH:10][C:15]([C:16]([OH:18])=[O:17])=[C:6]([Br:12])[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 133472764-Acetyl-2-bromobenzonitrile

Product 1

HCID 13347277HCID 13347277, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of the product obtained in step 2 (0.5 g, 2.23 mmol) in AcOH (2.5 mL), H2O (2.5 mL) and concentrated H2SO4 (2.5 mL) was refluxed for 5 h. After cooling, the reaction mixture was adjusted with 10 N NaOH to pH=10 and washed with AcOEt. The aqueous layer was acidified with concentrated HCl to pH=1 and then extracted with AcOEt. The organic phase was washed with H2O, dried over Na2SO4 and evaporated under reduced pressure. The crude product was used in the following step without further purification.

Workup

  1. temperatureAfter cooling
  2. washwashed with AcOEt
  3. extractionextracted with AcOEt
  4. washThe organic phase was washed with H2O
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure
  7. customThe crude product was used in the following step without further purification

Sources & evidence

ORD record
ord-c1267523512b47bb811029123f96d168
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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