Hydrogen Peroxide → 4-Chloro-3,5-difluoroaniline

HRID 2259533Notes

Reaction equation

HRID 2259533 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5](O)=[CH:4][C:3]=1[F:10].BrC1C=C(F)C(Cl)=C(F)C=1.C(OO)(C)(C)C.OO.ClC1C(F)=CC=CC=1F.FC1C=CC=C(F)C=1[NH2:41]>Cl>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH2:41])=[CH:4][C:3]=1[F:10]

Participants

8

Reactant 6

HCID 784Hydrogen PeroxideHCID 6410tert-Butyl hydroperoxideHCID 796472,6-DifluoroanilineHCID 142257Benzene, 2-chloro-1,3-difluoro-HCID 27732585-Bromo-2-chloro-1,3-difluorobenzeneHCID 194366204-Chloro-3,5-difluorophenol2×

Product 1

HCID 194366214-Chloro-3,5-difluoroaniline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Compound (250) can be prepared in the same manner as in Preparation Example 240, except for replacing compound (P102) with 4-chloro-3,5-difluorophenol. The 4-chloro-3,5-difluorophenol can be prepared by reacting a Grignard reagent prepared from 1-bromo-4-chloro-3,5-difluorobenzene with t-butyl hydroperoxide or converting the same Grignard reagent to a boric ester, and oxidizing the product with hydrogen peroxide under a basic condition. It is also prepared by nitrating 2-chloro-1,3-difluorobenzene (obtainable by decomposing a diazonium salt of 2,6-difluoroaniline in the presence of cuprous chloride or in hydrochloric acid), reducing the nitro-compound to obtain 4-chloro-3,5-difluoroaniline, and decomposing its diazonium salt in sulfuric acid.

Sources & evidence

ORD record
ord-1d1a709b043a4d45a68f0961ea7e2b42
Source dataset
uspto-grants-1995_12
Patent number
US05474707

Reaction notes

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