Hydrogen Peroxide → HCID 19032155, compound

HRID 2259534Notes

Reaction equation

HRID 2259534 reaction equation
FC1C=CC=C(F)C=1O.CCN(S(F)(F)F)CC.[F:19][C:20]1[CH:21]=[C:22]([OH:31])[CH:23]=[C:24]([F:30])[C:25]=1[O:26][CH:27]([F:29])[F:28].Br[C:33]1[CH:38]=[C:37]([F:39])[C:36]([O:40][CH:41]([F:43])[F:42])=[C:35]([F:44])[CH:34]=1.C(OO)(C)(C)C.OO>>[F:19][C:20]1[CH:21]=[C:22]([OH:31])[CH:23]=[C:24]([F:30])[C:25]=1[O:26][CH:27]([F:29])[F:28].[F:39][C:37]1[CH:38]=[CH:33][CH:34]=[C:35]([F:44])[C:36]=1[O:40][CH:41]([F:42])[F:43]

Participants

8

Reactant 6

HCID 784Hydrogen PeroxideHCID 6410tert-Butyl hydroperoxideHCID 943922,6-DifluorophenolHCID 123472(Diethylamino)sulfur trifluorideHCID 19032155HCID 19032155, compoundHCID 227175145-Bromo-2-(difluoromethoxy)-1,3-difluorobenzene

Product 2

HCID 19032155HCID 19032155, compoundHCID 195938212-(Difluoromethoxy)-1,3-difluorobenzene

Procedure

Compound (251) can be prepared in the same manner as in Preparation Example 248, except for replacing 3-fluoro-4-difluoromethoxyphenol with 3,5-difluoro-4-difluoromethoxyphenol. The 3,5-difluoro-4-difluoromethoxyphenol can be obtained by converting 2,6-difluorophenol to a formic ester, fluorinating the ester with DAST, brominating the resulting 2,6-difluoro-1-difluoromethoxybenzene, preparing a Grignard reagent from the resulting 4-bromo-2,6-difluoro-1-difluoromethoxybenzene, and reacting the Grignard reagent with t-butyl hydroperoxide or converting the Grignard reagent to a boric ester, and oxidizing the ester with hydrogen peroxide under a basic condition. Alternatively, 3,5-difluoro-4-difluoromethoxyphenol can also be obtained by nitrating 3,5-difluoro-4-difluoromethoxybenzene, reducing the product to 3-fluoro-4-trifluoromethoxyaniline, and decomposing a diazonium salt of the 3-fluoro-4-trifluoromethoxyaniline in sulfuric acid.

Sources & evidence

ORD record
ord-5986e219b93644da9d8bb62e0170853d
Source dataset
uspto-grants-1995_12
Patent number
US05474707

Reaction notes

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