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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 68565Generated: October 25, 2026

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

https://huagongshe.com/reaction/68565

Reaction equation

Participants

RoleNameHCIDCharge
Reactanttert-Butyl methyl etherHCID 15413—
ReactantLithium hydrideHCID 62714—
Reactant1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-oneHCID 2758231—
Reactant1-(4-Bromo-5-methyl-thiophen-2-yl)-ethanoneHCID 12682498—
SolventTetrahydrofuranHCID 8028—
Product(4-Bromo-5-methyl-thiophen-2-yl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-butan-1-oneHCID 86706646127.2%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08822466B2
Source datasetuspto-grants-2014_09
ORD IDord-256f1e9a4bc240aaa0a54cd7126c754c
Source noteuspto-grants-2014_09