Sodium Cyanide → HCID 53434575, compound

HRID 2240935Notes

Reaction equation

HRID 2240935 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([CH2:8][CH2:9][CH2:10]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:7]=1.[C-:23]#[N:24].[Na+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([CH2:8][CH2:9][CH2:10][C:23]#[N:24])[CH:7]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 59305329HCID 59305329, compound

Product 1

HCID 53434575HCID 53434575, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of Toluene-4-sulfonic acid 3-(5-bromo-2-fluoro-phenyl)-propyl ester (0.59 g, 1.5 mmol) in anhydrous DMSO (3.0 mL) was added sodium cyanide (0.112 g, 2.3 mmol) and heated to 80° C. for 12 h. The mixture was cooled and partitioned between ethyl acetate and H2O, and the aqueous layer was extracted with ethyl acetate (15 mL). The combined organic layers were washed with brine (1×15 mL), dried (MgSO4), filtered and concentrated under reduced pressure. Silica gel chromatography (10-20% Ethyl acetate/petroleum ether) gave the title compound as a clear oil (0.37 g, 99%), and was used directly in the next step.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between ethyl acetate and H2O
  3. extractionthe aqueous layer was extracted with ethyl acetate (15 mL)
  4. washThe combined organic layers were washed with brine (1×15 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-422ed9bc8935452eb224d62d382e23d9
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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