Methyl 4-bromobenzoate

Chemical properties

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The Uses of Methyl 4-bromobenzoate

Methyl 4-bromobenzoate is halogenated benzoate used as a reagent in organic synthesis. Methyl 4-bromobenzoate can be used to stimulate microbial dechlorination of PCBs. It is also used in the preparation of stable radioiodinating reagent to label monoclonal antibodies for radiotherapy of cancer.

The Uses of Methyl 4-bromobenzoate

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.

What are the applications of Application

Methyl 4-bromobenzoate may be used in the following syntheses:

1. Methyl 4-(2-pyridyl)benzoate by cross coupling reaction with lithium 2-pyridyltriolborate.
2. Methyl 4-imidazo[1,2-a]pyridin-3-ylbenzoate by ligand-free Pd(OAc)2 catalyzed reaction with Imidazo[1,2-a]pyridine.
3. 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′.

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.]