HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butyl methyl ether → 1-(5-Bromo-4-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-(5-Bromo-4-methylthiophen-2-yl)ethan-1-one | HCID 45480353 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-(5-Bromo-4-methyl-thiophen-2-yl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-butan-1-one | HCID 86658038 | 111.4% |
Reaction Steps
LiH (2.06 g) is added to a solution of 3′,5′-dichloro-2,2,2-trifluoroacetophenone (48.0 g) and 1-(5-bromo-4-methyl-thiophen-2-yl)-ethanone (30.3 g) in THF (1000 ml). After 2 hours at 60° C. MTBE is added (300 ml) and the reaction mixture is poured onto water (500 ml) at 0° C. The organic phase is extracted with water and a saturated aqueous solution of NaCl, dried over Na2SO4 and concentrated in vacuo to yield 71.2 g of 1-(5-bromo-4-methyl-thiophen-2-yl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one. The crude product is used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08383659B2 |
| Source dataset | uspto-grants-2013_02 |
| ORD ID | ord-69c159e3c01b4a2aa65b81fe1b2c91d9 |
| Source note | uspto-grants-2013_02 |