Synthesis of stable nitrile oxide compounds

A process for the synthesis of stable aryl nitrile oxides which comprises the sequential steps of (1) halomethylating a halomethyl group onto a substituted aromatic compound having at least one substituent group selected from the group consisting of alkyl groups, aryl groups, fused aryl groups, alkaryl groups, halogen atoms, alkoxy groups and nitro groups, wherein said halomethyl group is halomethylated onto a position that is ortho to at least one of the substituent groups on the substituted aromatic compound to produce an ortho halomethylated-substituted aromatic compound, wherein the substituted aromatic compound is halomethylated by allowing the substituted aromatic compound to react with a mixture of acetic acid, hydrogen bromide, and paraformaldehyde;

• (2) conveying the ortho halomethylated-substituted aromatic compound into an ortho-substituted aromatic aldehyde by reacting the ortho halomethylated-substituted aromatic compound with a salt selected from the group consisting of sodium 2-nitropropane and potassium 2-nitropropane in a lower alcohol solvent;
• (3) converting the ortho-substituted aromatic aldehyde into an ortho-substituted aromatic oxime by reacting the ortho-substituted aromatic aldehyde with hydroxylamine;
• and (4) converting the ortho-substituted aromatic oxime into the ortho-substituted aryl nitrile oxide by reacting the ortho-substituted aromatic oxime with an aqueous sodium hypochlorite solution at a temperature which is within the range of about −5° C. to about 20° C.