Iodine → HCID 67292422, compound

HRID 1685399Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.II.[Mg].[C:12]([C:14]1[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][N:15]=1)#N.S(=O)(=O)(O)[OH:22].[OH-].[Na+]>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]([C:14]2[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][N:15]=2)=[O:22])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 10 °C

Procedure

48.5 g (205.5 mM) of 1,4-dibromobenzene are added dropwise to a mixture containing one crystal of iodine and 5 g (205.5 mM) of magnesium metal covered with 150 ml of THF. The mixture is stirred at the reflux temperature of the solvent for 2 hours and then cooled to 10° C. 12.34 g (102.7 mM) of 2-cyano-3-pyridinol are then added dropwise. The reaction medium is heated at the reflux temperature of the solvent for 3 hours, then stirred for 18 h at room temperature and then treated with 300 ml of 0.5 N sulfuric acid. The solvents are driven off under reduced pressure and the residual aqueous phase is brought to pH 4 by adding a necessary and sufficient amount of 2 N sodium hydroxide solution. The neutralized mixture is extracted with dichloromethane and the organic phase is dried over magnesium sulfate. After evaporation of the solvent, the expected product is obtained in the form of a yellow solid with a yield of 35%.

Workup

temperatureThe reaction medium is heated at the reflux temperature of the solvent for 3 hours
stirringstirred for 18 h at room temperature
extractionThe neutralized mixture is extracted with dichloromethane
dry with materialthe organic phase is dried over magnesium sulfate
customAfter evaporation of the solvent

Sources & evidence

ORD record: ord-5138f20beedf431b96a033989ffd5101
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148407B2

Reaction notes

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