Bromotrimethylsilane → HCID 12968680, compound
Reaction equation
C[O:2][P:3]([CH2:7][NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])(=[O:6])[O:4]C.Br[Si](C)(C)C>C(Cl)Cl>[F:18][C:15]1[CH:14]=[CH:13][C:12]([S:9]([NH:8][CH2:7][P:3](=[O:2])([OH:6])[OH:4])(=[O:11])=[O:10])=[CH:17][CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of diester 35 (0.58 g, 1.95 mmol) in dry CH2Cl2 (10 mL) and bromotrimethylsilane (1.5 mL, 11.7 mmol) was stirred at room temperature for 5 hours and then concentrated. The resulting residue was dissolved in anhydrous CH3OH (10 mL) and stirred at room temperature for 20 minutes. Insolubles were filtered, and the filtrate was concentrated. Purification by trituration with CH2Cl2 gave the phosphonic acid (iv) (0.51 g, 97%) as a white solid: 1H NMR (300 MHz, CD3OD) δH 3.17 (d, J=13.5 Hz, 2H), 7.35 (m, 2H), 7.97 (m, 2H).