Water → 2-Bromo-4-methoxy-3-(4-nitrophenoxy)benzaldehyde

HRID 131584Notes

Reaction equation

[F-].[K+].[Br:3][C:4]1[C:11]([OH:12])=[C:10]([O:13][CH3:14])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.O>CS(C)=O>[Br:3][C:4]1[C:11]([O:12][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[C:10]([O:13][CH3:14])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

Conditions

Temperature: 140 °C

Procedure

To a stirred suspension of potassium fluoride (1.89 gm, 0.0326 mol) in dry DMSO (10 ml) was added a solution of 2-bromoisovanillin (5.0 gm, 0.0217 mol) in DMSO (10 ml). A solution of 4-fluoronitrobenzene (5.0 gm, 0.0260 mol) in DMSO (5 ml) was added to the above suspension and the reaction mixture was stirred at 140° C. for 4 h. The reaction mixture was cooled to room temperature and the contents were poured into water (150 ml) and extracted with ethyl acetate (50 ml×3). The organic extracts were combined and washed with 1N sodium hydroxide (25 ml×2), water and brine and dried over anhydrous sodium sulfate. The dried organic layer was concentrated in vacuo and the residue was purified by silica-gel column chromatography using 20% ethyl acetate-petroleum ether as the eluent to give 2-bromo-3-(p-nitrophenoxy)-4-methoxy benzaldehyde as a pale yellow solid (5.0 gm) mp: 132-140° C.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate (50 ml×3)
washwashed with 1N sodium hydroxide (25 ml×2), water and brine
dry with materialdried over anhydrous sodium sulfate
concentrationThe dried organic layer was concentrated in vacuo
customthe residue was purified by silica-gel column chromatography

Sources & evidence

ORD record: ord-7a935dba3ce549eea48a1b6f1eb78cf0
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384962B2

Reaction notes

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