Aniline → Aniline;2-bromoethylphosphonic acid
Reaction equation
C([O:3][P:4]([CH2:9][CH2:10][Br:11])(=[O:8])[O:5]CC)C.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>Br.C(O)C>[C:13]1([NH2:12])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Br:11][CH2:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of about 50 g of diethyl-2-bromoethyl-phosphonate in about 255 ml of about 48% hydrobromic acid was kept at reflux (about 95°-100° C.) overnight. The solvent was removed under reduced pressure and the residue evaporated twice with toluene, giving a syrup. This syrup was dissolved in about 65 ml of about 99% ethanol, about 20 g of aniline was added dropwise and the solid was collected, washed with cold about 99% ethanol (at about 0° C.) and dried in vacuo, giving about 30.6 g of the desired reagent, mp 157°-158° C.