HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-{[3-(Aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trimethylphosphine | HCID 68983 | — |
| Reactant | 3-{[3-(Azidomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile | HCID 86644925 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-{[3-(Aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile | HCID 67197166 | 79.7% |
Reaction Steps
Trimethylphosphine (1M in THF) (6.41 mL, 6.41 mmol) and water (0.384 mL, 21.36 mmol) were added to a solution of 3-{[3-(azidomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile (1.630 g, 4.27 mmol) in THF (30 mL) at RT. The mixture was stirred at RT overnight. The solvent was evaporated. The residue was purified by chromatography with dichloromethane:methanol to give the title compound (1.21 g, 79%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.80 (s, 1H), 7.60 (dd, 1H), 7.43-7.51 (m, 2H), 7.41 (t, 1H), 3.75 (s, 2H), 1.92 (br. s., 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08304419B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-c7696ed23204489f924a207964845ad2 |
| Source note | uspto-grants-2012_11 |