2,3,4-Trimethoxybenzoic acid → 5-Bromo-2,3,4-trimethoxybenzoic acid

HRID 1042726

Reaction equation

[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].CC([O-])=O.[Na+].[Br:21]Br>CC(O)=O.C(OCC)C>[Br:21][C:9]1[C:10]([O:14][CH3:15])=[C:11]([O:12][CH3:13])[C:3]([O:2][CH3:1])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2,3,4-trimethoxybenzoic acid (4.7 g, 22 mmol) and NaOAc (5.5 g, 40 mmol) in 35 ml AcOH was added a solution of bromine (1.5 ml, 29 mmol) in 35 ml AcOH. The reaction became red in color, which quickly faded. The mixture was heated to 80° C. for 1 h, at which point it was cooled to ambient temperature. The material was partitioned between dichloromethane and water. The organic layer was removed and the aqueous layer was extracted once with dichloromethane. The combined organic layers were dried with Na2SO4, filtered, and concentrated to give an oil which solidified on standing. The material was dissolved in diethyl ether and hexanes. Concentration to ½ the volume resulted in precipitation of a white solid. Filtration provided the title compound as a white solid. MS m/z: 293 (M+H+); calc'd for C10H11BrO5: 291.1

Workup

temperaturewas cooled to ambient temperature
customThe material was partitioned between dichloromethane and water
customThe organic layer was removed
extractionthe aqueous layer was extracted once with dichloromethane
dry with materialThe combined organic layers were dried with Na2SO4
filtrationfiltered
concentrationconcentrated
customto give an oil which
concentrationConcentration
customresulted in precipitation of a white solid
filtrationFiltration

Sources & evidence

ORD record: ord-86887e954fa04ebb8c437c66b3067012
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557996B2

Linked notes

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