Bromoacetonitrile → 4-(5-Chloro-2-hydroxy-phenyl)-4-oxo-butyronitrile

HRID 11728

Reaction equation

HRID 11728 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.COC(=O)[O-].[Mg+2].COC(=O)[O-].Br[CH2:24][C:25]#[N:26]>Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH2:9][CH2:24][C:25]#[N:26])[CH:7]=1

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 740613-Chloro-6-hydroxyacetophenoneHCID 167017Carbonic acid, monomethyl ester, magnesium salt (2:1)

Product 1

HCID 219733224-(5-Chloro-2-hydroxy-phenyl)-4-oxo-butyronitrileYield 58.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1-(5-chloro-2-hydroxy-phenyl)-ethanone (1.0 g, 5.86 mmol) and magnesium methylcarbonate (13 mL, 32.5 mmol, 2.5 M solution in DMF) was stirred at 120° C. for 3 hours. The mixture was cooled to ambient temperature followed by the addition of bromoacetonitrile (1.22 mL, 17.6 mmol). The resulting solution was stirred at 90° C. for 3 hours. The reaction was cooled to ambient temperature then slowly poured into 1 M hydrochloric acid (200 mL). This was extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, filtered and concentrated. Flash chromatography on silica gel gave the title compound (0.72 g).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. extractionThis was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-17531f7d84eb482b9d2cd0545ab98c03
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

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