Bromotrimethylsilane → [Bromo(Phenyl)Methyl]Phosphonic Acid
Reaction equation
[Br:1][CH:2]([P:9](=[O:14])([O:12]C)[O:10]C)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[Si](Br)(C)C>C(Cl)Cl>[Br:1][CH:2]([P:9](=[O:10])([OH:14])[OH:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5 (0.3 g, 1.08 mmol, 1 eq) was dissolved in dry DCM (5 mL). TMSBr (1.2 mL, 8.64 mmol, 8 eq) was added under an inert atmosphere. The reaction was stirred for 20 h at room temperature. The solvent was then evaporated, and MeOH (5 mL) was added to the reaction mixture and stirred for 1 h. The solvent was evaporated and the crude product was dissolved in water (5 mL), filtered and freeze dried yielding 7 as a white powder (229 mg, 85%). 1H NMR (400 MHz, D2O) δ 7.61-7.52 (m, 2H), 7.44-7.33 (m, 3H), 5.10-5.02 (m, 1H). 13C NMR (101 MHz, D2O) δ 136.49 (d, JC-P=3.3 Hz), 129.35 (d, JC-P=6.0 Hz), 129.09 (s), 43.54 (s). 31P NMR (162 MHz, D2O) δ 15.44 (s). ESIMS calculated for C7H7BrO3P [M-H]− 248.93, found: 248.93 mp 158-60° C.