Benzoic acid, 2-broMo-6-(broMoMethyl)-, Methyl ester

Benzoic acid, 2-broMo-6-(broMoMethyl)-, Methyl ester - Names and Identifiers

Name	methyl 2-bromo-6-(bromomethyl)benzoate
Synonyms	ethyl 2-bromo-6-(bromomethyl)benzoate methyl 2-bromo-6-(bromomethyl)benzoate METHYL 2-BROMO-6-(BROMOMETHYL)BENZOATE 2-Bromo-6-bromomethyl-benzoic acid methyl ester Benzoic acid, 2-broMo-6-(broMoMethyl)-, Methyl ester
CAS	777859-74-2

Benzoic acid, 2-broMo-6-(broMoMethyl)-, Methyl ester - Physico-chemical Properties

Molecular Formula	C9H8Br2O2
Molar Mass	307.97
Storage Condition	under inert gas (nitrogen or Argon) at 2-8°C

Benzoic acid, 2-broMo-6-(broMoMethyl)-, Methyl ester - Reference Information

synthesis

step 1: preparation of methyl 2-bromo -6-methylbenzoate
compound 9(40g,186mmol) is dissolved in sulfoxide chloride (54.3ml,744mmol), stirred and heated to about 80 ℃ in a 500mL pear flask, the reaction lasted about 3 hours. MeOH(200ml) is dropped into the solution in the ice bath through a dropping funnel, the obtained solution is stirred at about 80 ℃ for about 30 minutes, the reaction mixture is diluted with ethyl acetate, washed with saturated NaHCO 3, water and saturated NaCl, the combined organic layer is dried with anhydrous sodium sulfate, filtered and concentrated to obtain methyl 2-bromo-6-methylbenzoate. the reaction equation is as follows:
step 2: preparation of methyl 2-bromo-6-bromomethylbenzoate
The mixture of methyl 2-bromo-6-methylbenzoate (compound 10,2.50g,9.05mmol),N-bromosuccinimide (1.93g,10.86mmol) and azobisisobutyronitrile (0.669g,4.07mmol) in carbon tetrachloride (20mL) is refluxed and stirred overnight, and the mixture is vacuum concentrated, the residue is purified on a silica column (PE / EtOAc = 200:1,v / v) to obtain methyl 2-bromo-6-bromomethylbenzoate, which is a white solid (1.62g, yield 50%), The reaction equation is as follows:

Application

Methyl 2-bromo-6-bromomethylbenzoate can be used as a pharmaceutical intermediate to synthesize other compounds with certain activity. Examples of the application of methyl 2-bromo-6-bromomethylbenzoate are as follows:
The mixture of methyl 2-bromo-6-bromomethylbenzoate (0.71mmol) and 4-methoxy-3- [2-(4-methyl-piperidine-1-yl)-ethoxy]-aniline hydrochloride (1.5 equivalent) in anhydrous DMF(2ml) is heated to 150°C for 10 minutes in a microwave reactor. The mixture is vacuum concentrated, the residue is subjected to column chromatography, and then converted to hydrochloride to obtain a new compound with pharmacological activity, which can be used to treat CNS and other diseases.

Last Update：2024-04-09 15:16:37