HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butyl methyl ether → (4-Bromo-5-methyl-thiophen-2-yl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-butan-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butyl methyl ether | HCID 15413 | — |
| Reactant | Lithium hydride | HCID 62714 | — |
| Reactant | 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-one | HCID 2758231 | — |
| Reactant | 1-(4-Bromo-5-methyl-thiophen-2-yl)-ethanone | HCID 12682498 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (4-Bromo-5-methyl-thiophen-2-yl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-butan-1-one | HCID 86706646 | 127.2% |
Reaction Steps
LiH (3.2 g) is added to a solution of 1-(3,5-dichloro-phenyl)-2,2,2-trifluoro-ethanone (56 g) and 1-(4-bromo-5-methyl-thiophen-2-yl)-ethanone (41 g) in dry THF (500 ml). After 5 h at 60° C. under nitrogen atmosphere, tert-butylmethylether (500 ml) is added to the reaction mixture. The reaction is slowly quenched with water (500 ml) at 5° C. and further extracted twice with tert-butylmethylether (500 ml). The organic phases are combined, washed with a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo to yield 1-(4-bromo-5-methyl-thiophen-2-yl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-butan-1-one (110 g, 77% purity) as a brown oil. The crude product is used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822466B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-256f1e9a4bc240aaa0a54cd7126c754c |
| Source note | uspto-grants-2014_09 |