HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 6-Bromo-4-(3-chloropropyl)-8-fluoro-4H-benzo[1,4]oxazin-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-Chloro-3-iodopropane | HCID 81363 | — |
| Reactant | 6-bromo-8-fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one | HCID 46856463 | — |
| Solvent | Ethylacetate heptane | HCID 21899848 | — |
| Product | 6-Bromo-4-(3-chloropropyl)-8-fluoro-4H-benzo[1,4]oxazin-3-one | HCID 68911140 | 72.1% |
Reaction Steps
6-Bromo-8-fluoro-4H-benzo[1,4]oxazin-3-one (95MF44) (0.091 g, 0.37 mmol), Cs2CO3 (0.180 g, 0.55 mmol) and 3-chloro-1-iodopropane (0.083 g, 0.41 mmol) were mixed according to GP5. CC (SiO2; Heptane/EtOAc 9:1-4) gave the title compound (95MF50(2084)) (0.086 g, 72%). 1H NMR (CDCl3) δ 7.02-6.96 (m, 1H), 6.85 (d, J=5.2 Hz, 1H), 4.65 (s, 2H), 4.04-4.11 (m, 2H), 3.62 (t, J=6.2 Hz, 2H), 2.10-2.18 (m, 2H); 13C NMR (CDCl3) δ 163.8, 151.7 (d, J=250.9 Hz), 133.1 (d, J=14.6 Hz), 131.5 (d, J=3.8 Hz), 115.1 (d, J=21.5 Hz), 114.2 (d, J=10.0 Hz), 113.4 (d, J=3.4 Hz), 67.6, 42.2, 39.5, 30.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07576100B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-754d6714594c4a56b3a7382b2e148f23 |
| Source note | uspto-grants-2009_08 |