Acetone → 4,5-dibromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxylic acid

HRID 251963Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[O:16])[N:5]([C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[C:6]=1[Br:7].CC(C)=[O:19].[Mn]([O-])(=O)(=O)=O.[K+]>O>[Br:1][C:2]1[CH:3]=[C:4]([C:15]([OH:19])=[O:16])[N:5]([C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[C:6]=1[Br:7]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 1.0 g of 4,5-dibromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carbaldehyde, 15 ml of acetone and 7 ml of water was slowly added 1.3 g of potassium permanganate at 40° C. The resulting mixture was stirred at 60° C. for 2 hours. Precipitates in the reaction mixture were removed by filtration. The resulting filtrate was washed with chloroform two times. The aqueous layer was adjusted to around pH 3 by an addition of 2N hydrochloric acid and then extracted with ethyl acetate three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 0.69 g of 4,5-dibromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxylic acid of the formula:

Workup

customat 40° C
customPrecipitates in the reaction mixture
customwere removed by filtration
washThe resulting filtrate was washed with chloroform two times
additionThe aqueous layer was adjusted to around pH 3 by an addition of 2N hydrochloric acid
extractionextracted with ethyl acetate three times
washwashed with an aqueous saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d230ad2275694666b3c5b697ba7d4dea
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07867949B2

Reaction notes

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