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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 732237Generated: October 27, 2026

Boron trifluoride → 4-(5-Isopropyl-2-Methyl-1,3-Thiazol-4-Yl)-Phenol

https://huagongshe.com/reaction/732237

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBoron trifluorideHCID 6356—
ReactantSodium CyanideHCID 8929—
ReactantBromic acidHCID 24445—
Reactant5-Isopropyl-4-(4-Methoxy-Phenyl)-2-Methyl-1,3-ThiazoleHCID 57838363—
CatalystTetrabutylammonium IodideHCID 67553—
SolventAcetic AcidHCID 176—
SolventDimethyl SulfoxideHCID 679—
SolventDiethyl EtherHCID 3283—
Product4-(5-Isopropyl-2-Methyl-1,3-Thiazol-4-Yl)-PhenolHCID 16202444—

Reaction Steps

In the fourth step, the compound (5) prepared in the third step is reacted with bromic acid and acetic acid, sodium cyanide and dimethylsulfoxide, or tetrabutylammonium iodide and boron trifluoride.diethylether, to afford 4-(5-isopropyl-2-methyl-1,3-thiazol-4-yl)-phenol (6). Conventionally, ethanethiol is used, whereby offensive odors occur and reagent handling is difficult to the extent of being unsuitable for use in mass production. However, in the present invention, the use of the compound (5) and the above materials reacting therewith, in particular, bromic acid and acetic acid result in decreased offensive odors, low price, simple reagent handling and a drastically increased preparation yield (yield: 84%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07585979B2
Source datasetuspto-grants-2009_09
ORD IDord-125362ffe0174e0bb4b5bb8def022a0f
Source noteuspto-grants-2009_09