Thionyl Chloride → 4-[5-(chloromethyl)-1H-tetrazol-1-yl]-2-(trifluoromethyl)benzonitrile
Reaction equation
O[CH2:2][C:3]1[N:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[N:6]=[N:5][N:4]=1.S(Cl)([Cl:22])=O>C1(C)C=CC=CC=1>[Cl:22][CH2:2][C:3]1[N:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[N:6]=[N:5][N:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-2-(trifluoromethyl)benzonitrile (Intermediate 23, 30.0 g) in toluene (500 mL) was added thionyl chloride (14.5 g, 0.122 mol) at room temperature. The reaction was heated to reflux and stirred for 2 hours. The reaction mixture was concentrated under vacuum and diluted with DCM. The resulting solution was washed with ice-water, followed by aqueous NaHCO3. The organic was separated and washed with brine solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by triturating with ether (500 mL) and dried under vacuum to yield 4-[5-(chloromethyl)-1H-tetrazol-1-yl]-2-(trifluoromethyl)benzonitrile (23 g).