Bromotrimethylsilane → HCID 22179271, compound

Participants

Reaction Steps

To a solution of [(2-thiophenesulfonyl-N-methylamino)methyl]-phosphonic acid dimethyl ester (obtained as described in Example 46, step 2) (180 mg, 0.6 mmol) in dichloromethane (3 mL) at 0° C. was slowly added bromotrimethylsilane (190 μL, 1.4 mmol). The reaction was gradually warmed to room temperature and allowed to stir overnight. The reaction mixture was concentrated, the residue was redissolved in dichloromethane, and the solution was again concentrated. Methanol (10 mL) was added to the residue, and the solution was stirred at room temperature for 30 min. The solution was then filtered and concentrated. The oily residue was triturated with 1:1 ether-hexanes, and an orange solid was collected by filtration. The orange solid was boiled in dichloromethane (3 mL), cooled, and filtered to yield the title compound (120 mg, 74%) as a colorless solid: 1H NMR (400 MHz, CD3OD) δH 7.87 (dd, J=1.5, 4 Hz, 1H, Ar—H, 7.66 (dd, J=1.5, 3.5 Hz, 1H, Ar—H, 7.25 (dd, J-4, 5 Hz, 1H, Ar—H), 3.31 (d, J=12.5 Hz, 2H, CH2P), 2.92 (s, 3H, NCH3).

Provenance & Evidence