1,3-Dichloroacetone → (E)-4-chloromethyl-2-[2-(2,4-difluorophenyl)ethenyl]oxazole

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]([NH2:13])=[O:12].[Cl:14][CH2:15][C:16]([CH2:18]Cl)=O>>[Cl:14][CH2:15][C:16]1[N:13]=[C:11](/[CH:10]=[CH:9]/[C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[O:12][CH:18]=1

Participants

Reactant 2

HCID 107931,3-Dichloroacetone

HCID 22259318(2E)-3-(2,4-Difluorophenyl)prop-2-enamide

Product 1

HCID 12109498(E)-4-chloromethyl-2-[2-(2,4-difluorophenyl)ethenyl]oxazoleYield 49.4%

Procedure

Using (E)-3-(2,4-difluorophenyl)-2-propenamide (9.16 g) and 1,3-dichloroacetone (7.62 g), the same reaction as Reference Example 1-(ii) was carried out to yield the titled compound (6.31 g) as colorless crystals.

Workup

customthe same reaction as Reference Example 1-(ii)

Sources & evidence

ORD record: ord-d19ba9a426f843648c0b0c01d5c4e91b
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06984653B2

Reaction notes

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