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

HRID 732237

Reaction equation

HRID 732237 reaction equation
[CH:1]([C:4]1[S:8][C:7]([CH3:9])=[N:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=1)([CH3:3])[CH3:2].Br(O)(=O)=O.[C-]#N.[Na+].B(F)(F)F>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C.CS(C)=O.C(O)(=O)C>[CH:1]([C:4]1[S:8][C:7]([CH3:9])=[N:6][C:5]=1[C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1)([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 6356Boron trifluorideHCID 8929Sodium CyanideHCID 24445Bromic acidHCID 578383635-Isopropyl-4-(4-Methoxy-Phenyl)-2-Methyl-1,3-Thiazole

Product 1

HCID 162024444-(5-Isopropyl-2-Methyl-1,3-Thiazol-4-Yl)-Phenol

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

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%).

Sources & evidence

ORD record
ord-125362ffe0174e0bb4b5bb8def022a0f
Source dataset
uspto-grants-2009_09
Patent number
US07585979B2

Linked notes

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