Hydrochloric Acid → HCID 18314511, compound

HRID 259680Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[Mg].[Cl:11][C:12]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:13]=1[CH:14]=[O:15].Cl>CCOCC.O1CCCC1>[Cl:11][C:12]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:13]=1[CH:14]([OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-bromoanisole (50 g, 0.267 mol) in ether is added portionwise to a mixture of magnesium (7.1 g, 0.293 mol) in ether. After the addition is complete, the reaction mixture is heated at reflux for 1 hour, diluted with ether, cooled to 0° C., treated with a solution of 2-chloro-5-nitrobenzaldehyde (39 g, 0.210 mol) in tetrahydrofuran, warmed to room temperature and diluted with an ice/water mixture. After acidifying the aqueous mixture with hydrochloric acid (pH2-pH3), the organic phase is separated and the aqueous phase is extracted with ether. The extracts are combined, washed sequentially with 10% sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title product as a brown gum.

Workup

additionAfter the addition
temperaturethe reaction mixture is heated
temperatureat reflux for 1 hour
temperaturewarmed to room temperature
customthe organic phase is separated
extractionthe aqueous phase is extracted with ether
washwashed sequentially with 10% sodium hydrogen carbonate solution and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-03d3dfde13c5439794b686c56c2a092a
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05523278

Reaction notes

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