4-Bromo-3,5-dimethyl-benzoic acid methyl ester

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4-Bromo-3,5-dimethyl-benzoic acid methyl ester Basic information
Product Name:4-Bromo-3,5-dimethyl-benzoic acid methyl ester
Synonyms:BENZOIC ACID, 4-BROMO-3,5-DIMETHYL-, METHYL ESTER;Mehtyl 4-broMo-3,5-diMethylbenzoate;Methyl 4-Bromo-3, 5-Dimethyl Benzoat;4-bromo-3,5-dimethyl benzoate;4-Bromo-3,5-dimethyl-benzoic acid methyl ester
CAS:432022-88-3
MF:C10H11BrO2
MW:243.1
EINECS:
Product Categories:
Mol File:432022-88-3.mol
4-Bromo-3,5-dimethyl-benzoic acid methyl ester Structure
4-Bromo-3,5-dimethyl-benzoic acid methyl ester Chemical Properties
Boiling point 310.8±37.0 °C(Predicted)
density 1.380±0.06 g/cm3(Predicted)
storage temp. Store at room temperature
solubility Chloroform (Slightly), Methanol (Slightly)
form Solid
color Off-White to Pale Beige
Safety Information
MSDS Information
4-Bromo-3,5-dimethyl-benzoic acid methyl ester Usage And Synthesis
UsesMethyl 4-Bromo-3,5-dimethylbenzoate is a useful reagent for the preparation of benzylaminopyrazinylcyclopropanecarboxylic acid derivatives for use as GPR40 receptor activity modulators.
Synthesis
Methanol

67-56-1

2-chloro-5-nitropyrimidine

400822-47-1

4-BROMO-3,5-DIMETHYL-BENZOIC ACID METHYL ESTER

432022-88-3

To a 250 mL round-bottomed flask was added 4-bromo-3,5-dimethylbenzaldehyde (4.0 g, 19 mmol), methanol (100 mL) and potassium iodide (623 mg, 3.8 mmol). The reaction mixture was stirred at 50 °C, followed by slow dropwise addition of tert-butyl hydroperoxide (3.9 mL, 70% aqueous solution, 28 mmol) over 30 min. After the dropwise addition, the reaction mixture was heated to reflux for 24 hours. After completion of the reaction, it was cooled to room temperature and the reaction was quenched by the addition of saturated aqueous sodium thiosulfate. The reaction mixture was extracted with ethyl acetate and the organic phase was dried with anhydrous sodium sulfate and subsequently concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using petroleum ether/ethyl acetate (15:1, v/v) as eluent to afford methyl 4-bromo-3,5-dimethylbenzoate as a white solid (3.8 g, 84% yield).1H NMR (400 MHz, CDCl3) δ 7.73 (s, 2H), 3.90 (s, 3H), 2.46 (s, 6H).

References[1] Dyes and Pigments, 2018, vol. 155, p. 323 - 331
4-Bromo-3,5-dimethyl-benzoic acid methyl ester Preparation Products And Raw materials
Raw materials2-chloro-5-nitropyrimidine-->4-Amino-3,5-dimethyl-benzoic acid methyl ester-->2,5-Dibromo-m-xylene-->Methanol-->tert-Butyl hydroperoxide-->2,4,6-Trimethybromombenzene
Tag:4-Bromo-3,5-dimethyl-benzoic acid methyl ester(432022-88-3) Related Product Information
p-Toluic acid 4-Bromo-3,5-dimethyl-benzoic acid methyl ester (4-Bromo-3-methylphenyl)methanol 4-Bromo-3-methylbenzoic acid Methyl 4-bromo-3-methylbenzoate 2-chloro-5-nitropyrimidine