ChemicalBook CAS DataBase List 4-(METHYLSULFONYL)BENZONITRILE

4-(METHYLSULFONYL)BENZONITRILE synthesis

13synthesis methods

Product Name:4-(METHYLSULFONYL)BENZONITRILE
CAS Number:22821-76-7
Molecular formula:C8H7NO2S
Molecular Weight:181.21

5398-77-6 Synthesis

5398-77-6
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$11.00/25g

22821-76-7
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$8.00/1g

Yield: 81%

Reaction Conditions:

with trifluorormethanesulfonic acid;trimethylsilylazide in acetonitrile at 20; for 0.75 h;Sealed tube;Inert atmosphere;Schmidt Reaction;

Steps:

3.3. General Procedure A for the Synthesis of Aromatic Nitriles
General procedure: To a solution of an aromatic aldehyde 1 (0.500 mmol, 1.0 equiv) and TMSN3 (115 mg, 1.00 mmol,2.0 equiv) in a premixed HFIP/ACN mixture (2.0 mL, 1:1) in a nitrogen-flushed two dram vial wasadded triflic acid (TfOH; 17.7 L, 0.200 mmol, 0.40 equiv) (exotherm and brisk effervescence due tonitrogen gas evolution was immediately observed). The vial was capped and the reaction mixture wasallowed to stir at rt for 20-75 min. The reaction mixture was concentrated under nitrogen. The residueobtained was suspended in CH2Cl2/hexanes mixture and loaded on a silica gel in a 5 g samplecartridge. Purification using a normal phase silica flash column on a CombiFlash purification systemafforded a corresponding aromatic nitrile 2 upon concentration of appropriate fractions.

References:

Motiwala, Hashim F.;Yin, Qin;Aubé, Jeffrey [Molecules,2016,vol. 21,# 1,art. no. 45]