3-BROMO-4-IODOBENZOIC ACID METHYL ESTER Chemical Properties

Melting point:

56-60°C

Boiling point:

328.1±27.0 °C(Predicted)

Density 

2.059±0.06 g/cm3(Predicted)

Flash point:

>110℃

storage temp. 

2-8°C

form 

solid

color 

Light yellow to orange

InChI

InChI=1S/C8H6BrIO2/c1-12-8(11)5-2-3-7(10)6(9)4-5/h2-4H,1H3

InChIKey

OIMBMPVAESWCEA-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(I)C(Br)=C1

Safety Information

WGK Germany 

3

HS Code 

2916310090

3-BROMO-4-IODOBENZOIC ACID METHYL ESTER Usage And Synthesis

Uses

3-Bromo-4-iodobenzoic acid methyl ester is a reactant used in the preparation of selective inhibitors.

Synthesis

The general procedure for the synthesis of methyl 3-bromo-4-iodobenzoate from methyl 4-amino-3-bromobenzoate was as follows: methyl 4-amino-3-bromobenzoate (5.0 g, 22.0 mmol, purchased from Aldrich) was dissolved in acetone (35 mL), followed by the addition of 6 M hydrochloric acid (35 mL). The reaction mixture was cooled to 0 °C and sodium nitrite (NaNO2, 1.84 g, 26.1 mmol) dissolved in 10 mL of water was added dropwise. After stirring the reaction mixture at 0 °C for 2 h, potassium iodide (KI, 5.47 g, 32.6 mmol) dissolved in 20 mL of water was added slowly. The reaction mixture was gradually warmed to room temperature and stirring was continued for 1 hour. Upon completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate (EtOAc, 2 x 150 mL). The organic phases were combined and dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under vacuum. The residue was purified by column chromatography (using an 80 g Redi-Sep column) with the eluent gradually adjusted from 100% heptane to 20:80 ethyl acetate:heptane, resulting in the target product methyl 3-bromo-4-iodobenzoate (4.1 g, 55% yield) as a solid. The 1H NMR (CDCl3) data of the product were as follows: δ 8.27 (1H), 7.98 (1H), 7.64 (1H), 3.94 (3H).

References

[1] Angewandte Chemie - International Edition, 2008, vol. 47, # 42, p. 8108 - 8111
[2] Patent: US2012/232026, 2012, A1. Location in patent: Paragraph 0440; 0441
[3] Patent: US2012/35122, 2012, A1. Location in patent: Paragraph 0760; 0761
[4] Organic and Biomolecular Chemistry, 2012, vol. 10, # 25, p. 4907 - 4915

3-BROMO-4-IODOBENZOIC ACID METHYL ESTER(249647-24-3)Related Product Information

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