Sodium Cyanide → HCID 53434575, compound
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.