4-Iodotoluene → N,N-diethyl-m-toluidine

Reaction equation

[CH2:1]([N:3]([Sn](CCCC)(CCCC)CCCC)[CH2:4][CH3:5])[CH3:2].I[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:1]([N:3]([C:21]1[CH:22]=[C:23]([CH3:26])[CH:24]=[CH:25][CH:20]=1)[CH2:4][CH3:5])[CH3:2]

Participants

Procedure

Analogous reaction of N,N-diethylaminotributyltin with aromatic iodides were less efficient; however, satisfactory yields (>60% yields of isolated product) could be obtained in the presence of ammonium salts. Thus, the reaction of N,N-diethylaminotributyltin with p-iodotoluene in the presence of N-benzyltriethylammonium chloride in toluene at 100° C. afforded 3-(N,N-diethylamino)toluene in 63% isolated yield.