Bromotrimethylsilane → HCID 415022, compound

4 (0.15 g, 0.69 mmol, 1 eq) was dissolved in dry DCM (5 mL). TMSBr (0.77 mL, 5.52 mmol, 8 eq) was added to the solution 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 6 as a white powder (130 mg, 70%). 1H NMR (400 MHz, D2O) δ 7.52-7.31 (m, 5H), 4.99 (d, J=12.3 Hz, 1H). 13C NMR (101 MHz, D2O) δ 137.45, 128.78 (d, JC-P=2.3 Hz), 128.52 (d, JC-P=2.9 Hz), 127.39 (d, JC-P=5.7 Hz), 71.02 (d, JC-P=158.3 Hz). 31P NMR (162 MHz D2O) δ 20.98 (s). ESIMS calculated for C-7H9O4PNa [M+Na]+211.01, found: 211.02; mp 160-162° C.

1. customThe solvent was then evaporated
2. additionMeOH (5 mL) was added to the reaction mixture
3. stirringstirred for 1 h
4. customThe solvent was evaporated
5. dissolutionthe crude product was dissolved in water (5 mL)
6. filtrationfiltered
7. customfreeze dried

ORD record

ord-17aab84dd7624d0b9df56fefec4f3ea6

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09399653B2