2-Bromoanisole → HCID 15871310, compound

HRID 1279276Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Mg]Br.BrC1C=CC=CC=1[O:18]C.[Mg].[NH2:21][C:22]1[N:26]([C:27]2[C:32]([Cl:33])=[CH:31][C:30]([Cl:34])=[CH:29][C:28]=2[Cl:35])[N:25]=[C:24]([S:36][CH3:37])[C:23]=1[C:38]#N.[Cl-].[NH4+]>CCOCC>[NH2:21][C:22]1[N:26]([C:27]2[C:32]([Cl:33])=[CH:31][C:30]([Cl:34])=[CH:29][C:28]=2[Cl:35])[N:25]=[C:24]([S:36][CH3:37])[C:23]=1[C:38](=[O:18])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 2-methoxyphenylmagnesium bromide prepared from 18.7 g (0.10 mol) of 2-bromoanisole and 2.43 g (0.10 mol) of magnesium turnings in ether under dry nitrogen was added 1.6 g (5.0 mmol) of 5-amino-4-cyano-3-methylthio-1-(2,4,6-trichlorophenyl)pyrazole and the resulting mixture was stirred and refluxed for 16 hours. Upon cooling, the reaction was decomposed with 50 mL of saturated ammonium chloride solution. The organic phase was extracted with aqueous hydrogen chloride and the acidic extract was treated with 10 mL of concentrated hydrogen chloride and heated at 80-90° C. for 10 minutes after which the mixture was cooled and made alkaline. Extraction with methylene dichloride and chromatography of the extracts with mixtures of hexane and ethyl acetate gave 313 mg (14%) of the title compound, m.p. 200-202° C.

Workup

temperaturerefluxed for 16 hours
temperatureUpon cooling
extractionThe organic phase was extracted with aqueous hydrogen chloride
extractionthe acidic extract
additionwas treated with 10 mL of concentrated hydrogen chloride
temperaturewas cooled
extractionExtraction with methylene dichloride and chromatography of the extracts with mixtures of hexane and ethyl acetate

Sources & evidence

ORD record: ord-6418be1f4fd74c2d880fee6db7350c27
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448265B1

Reaction notes

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