ChemicalBook CAS DataBase List 4-BROMO-2-CHLOROBENZOIC ACID METHYL ESTER

4-BROMO-2-CHLOROBENZOIC ACID METHYL ESTER synthesis

7synthesis methods

Product Name:4-BROMO-2-CHLOROBENZOIC ACID METHYL ESTER
CAS Number:185312-82-7
Molecular formula:C8H6BrClO2
Molecular Weight:249.49

59748-90-2

4-BROMO-2-CHLOROBENZOIC ACID METHYL ESTER

185312-82-7

A. Methyl esterification: Dry hydrogen chloride gas was passed into a 100 ml methanol solution containing 10 g (42.5 mmol) of 4-bromo-2-chlorobenzoic acid until the solution began to reflux. The reaction mixture was stirred at room temperature overnight. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming that the reaction was essentially complete, the reaction mixture was concentrated under reduced pressure to give the crude product. The crude product was redissolved in ether and washed sequentially with deionized water (twice) and saturated sodium chloride solution. The organic phase was dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to afford 10 g of the light tan oily target product methyl 2-chloro-4-bromobenzoate in 94% yield.

59748-90-2 Synthesis

59748-90-2
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185312-82-7
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Yield: 94%

Reaction Conditions:

with hydrogenchloride in methanol;diethyl ether

Steps:

3.A A.
A. 4-Bromo-2-chloro benzoic acid, methyl ester Hydrochloric acid (gas) was bubbled through a solution of 10 g (42.5 mmol) of 4-bromo-2-chloro benzoic acid in 100 ml of methanol until reflux occurred. The resulting reaction mixture was allowed to react overnight. When the reaction was substantially complete, as indicated by TLC, the reaction mixture was concentrated in vacuo to provide a residue. This residue was redissolved in diethyl ether and washed sequentially with water (twice) and a saturated sodium chloride solution, dried over sodium sulfate, filtered and then concentrated in vacuo to provide 10 g of a light tan oil. Yield: 94%.

References:

Eli Lilly and Company US5786325, 1998, A

59748-90-2 Synthesis

59748-90-2
288 suppliers
$8.00/1g