2,6-Dichlorobenzaldehyde → 4-[(E)-2-(2,6-dichlorophenyl)-vinyl]-3-nitrobenzoic acid methyl ester

HRID 1514941Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:35][C:36]1[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[C:37]=1[CH:38]=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:38]/[C:37]2[C:36]([Cl:35])=[CH:43][CH:42]=[CH:41][C:40]=2[Cl:44])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 4-bromomethyl-3-nitrobenzoic acid methyl ester (1.89 g, 6.9 mmol) and Ph3P (1.82 g, 6.9 mmol) in DMF (35 mL) was heated at 100° C. for 1 h then 2,6-dichlorobenzaldehyde (1.2 g, 6.9 mmol) was added followed by K2CO3 (1.9 g, 13.75 mmol). The resulting deep-red mixture was stirred at 100° C. for 18 h then was allowed to cool to ambient temperature. To this was added water and the mixture was extracted with EtOAc. The organic phase was washed with water (3×) and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by chromatography using methylene chloride as eluent to give 4-[(E)-2-(2,6-dichlorophenyl)-vinyl]-3-nitrobenzoic acid methyl ester as a pale-yellow solid.

Workup

temperatureto cool to ambient temperature
extractionthe mixture was extracted with EtOAc
washThe organic phase was washed with water (3×)
dry with materialdried over sodium sulfate
customThe solvent was removed under reduced pressure
customthe residue was purified by chromatography

Sources & evidence

ORD record: ord-970308fb518a4047a8f7006d07b162de
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222248B2

Reaction notes

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