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

HRID 732237

반응식

HRID 732237 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 67553Tetrabutylammonium Iodide촉매HCID 176Acetic Acid용매HCID 679Dimethyl Sulfoxide용매HCID 3283Diethyl Ether용매

실험 절차

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%).

출처 및 근거

ORD 기록
ord-125362ffe0174e0bb4b5bb8def022a0f
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585979B2

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