Methyl 2-bromo-3,5-dimethoxybenzoate → 4,6,4',6'-Tetramethoxy-biphenyl-2,2'-dicarboxylic acid dimethyl ester

HRID 72001Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([O:12][CH3:13])[C:5]=1Br>CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1[C:5]([C:9]2[C:4]([C:3]([O:2][CH3:1])=[O:15])=[CH:5][C:6]([O:12][CH3:13])=[CH:7][C:8]=2[O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)=[O:15]

Participants

Conditions

Temperature: 150 °C

Procedure

2-Bromo-3,5-dimethoxy-benzoic acid methyl ester (5.2 g) was dissolved in DMF (16 mL), and Cu powder (2.4 g) was added. After stirring at 150° C. for 3 days, the mixture was filtered and evaporated under vacuum. The crude material was subjected to silica gel chromatography using effluent of 30-60% ethyl acetate and hexanes. The fractions containing product were combined and the solvent was removed under reduced pressure to provide 4,6,4′,6′-tetramethoxy-biphenyl-2,2′-dicarboxylic acid dimethyl ester (2.5 g, 68%) as a clear oil.

Workup

filtrationthe mixture was filtered
customevaporated under vacuum
additionThe fractions containing product
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-c99bab1b0302471e9424c410c768a20b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822430B2

Reaction notes

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