Chemical Properties
WHITE CRYSTALS OR CRYSTALLINE POWDER
Uses
Methyl 4-bromobenzoate is used as a starting material in the synthesis of three-carbon-bridged 5-substituted furo[2,3-d]pyrimidine and 6-substituted pyrrolo[2,3-d]pyrimidine and methyl 4-tri-n-butylstannylbenzoate. It is also used to stimulate microbial dechlorination of polychlorinated biphenyls. Further, it is used in the preparation of stable radioiodinating reagent to label monoclonal antibodies for radiotherapy of cancer.
Uses
Methyl 4-bromobenzoate is a halogenated benzoate used as a reagent in organic synthesis. It can be used to stimulate microbial dechlorination of PCBs. By condensing methyl 4-bromobenzoate with 3-buten-1-ol, 4-(4-methylphenyl)butanal can be obtained.
Application
Methyl 4-bromobenzoate may be used in the following syntheses:
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Methyl 4-(2-pyridyl)benzoate by cross coupling reaction with lithium 2-pyridyltriolborate.
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Methyl 4-imidazo[1,2-a]pyridin-3-ylbenzoate by ligand-free Pd(OAc)2 catalyzed reaction with Imidazo[1,2-a]pyridine.
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Methyl (E)-4-[3-(2-methoxycarbonylvinyl)-thiophen-2-yl]acrylate by reacting with methyl (E)-3-(thiophen-3-y)lacrylate.
General Description
Methyl 4-bromobenzoate is a
para-substituted aryl bromide. Mol-ecules of methyl 4-bromobenzoate are almost planar. The compound is isostructural with methyl 4-iodo-benzoate. The Zeeman effect on the N.Q.R. (nuclear quadrupole resonance) of methyl 4-bromobenzoate on single crystals, has been investigated by the ′geometric method′.
Synthesis
To a 25 mL reaction flask were sequentially added magnets, 1 mmol 1-bromo-4-(methoxymethyl)benzene (214 mg), 15 mg20 mol%
AgI/BiVO4 composite and 2 mL of water, equipped with a 28 cm diameter oxygen sphere, and a 16 W white light lamp 10 cm to the right of the reaction vial, the reaction system was irradiated by a 16
W white light lamp, the reaction system was reacted under the irradiation of 16 for 15 .
h, the reaction solution was extracted, the combined organic layers were washed three times with saturated brine, dried with anhydrous sodium sulfate, desolvated under reduced pressure, and the residue was processed by column chromatography (ethyl acetate/petroleum ether=1:10) to give methyl p-bromobenzoate in 88% yield
(188.7 mg).
Purification Methods
Crystallise the ester from MeOH. EtOH (m 81o, also 80.5o, 79.5o) or *C6H6/pet ether (m 78-79o). [Beilstein 9 H 352, 9 III 1405, 9 IV 1017.]
