Hydrochloric Acid → 3-[4-(Methanesulfonyl)phenyl]-3-oxopropanenitrile

HRID 133507Notes

Reaction equation

HRID 133507 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](Br)=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C-:15]#[N:16].[K+].Cl.C([OH:21])C>O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:21])[CH2:12][C:15]#[N:16])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 9032Potassium CyanideHCID 85854392HCID 85854392, compound

Product 1

HCID 150101063-[4-(Methanesulfonyl)phenyl]-3-oxopropanenitrileYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of 1.0 g (3.61 mmol) (4-methanesulfonyl-phenyl)-acetyl bromide in 15 ml ethanol was added a solution of 0.47 g (7.22 mmol) potassium cyanide in 5 ml water. The mixture was then stirred at RT for 1 h, then acidified to ph=5-6 with aqueous HCl 1M and then extracted with ethyl acetate, The combined organic phases were dried over sodium sulfate and concentrated in vacuo to afford 0.29 g (37%) 3-(4-methanesulfonyl-phenyl)-3-oxo-propionitrile as a yellow solid. ES-MS m/e (%): 222 (M, 100).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-145ddeb8385a450d8952efcc23ece01b
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Reaction notes

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