ChemicalBook CAS DataBase List METHYL 5-BROMO-2-HYDROXY-4-METHOXYBENZOATE

METHYL 5-BROMO-2-HYDROXY-4-METHOXYBENZOATE synthesis

4synthesis methods

Product Name:METHYL 5-BROMO-2-HYDROXY-4-METHOXYBENZOATE
CAS Number:39503-52-1
Molecular formula:C9H9BrO4
Molecular Weight:261.07

98437-41-3

18107-18-1

39503-52-1

A) General procedure for synthesizing methyl 5-bromo-2-hydroxy-4-methoxybenzoate: to a solution of 5-bromo-2-hydroxy-4-methoxybenzoic acid (2.00 g) in methanol (10.0 mL) was slowly added a solution of 0.6 M (diazomethyl)trimethylsilane in hexanes (14.8 mL) under cooling conditions in an ice bath. The reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, acetic acid (0.12 mL) was added to quench the reaction, followed by evaporation of the solvent under reduced pressure. The resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to afford the target compound methyl 5-bromo-2-hydroxy-4-methoxybenzoate (2.08 g). The product was characterized by 1H NMR (300 MHz, CDCl3) with chemical shifts of δ3.91 (3H, s), 3.93 (3H, s), 6.49 (1H, s), 7.99 (1H, s), 10.93 (1H, s).

98437-41-3 Synthesis

98437-41-3
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$125.00/1g

39503-52-1
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$18.00/100mg

Yield:39503-52-1 456 mg

Reaction Conditions:

with sulfuric acid in methanol at 70; for 24 h;

Steps:

12

Taking compound 2 d (1.0 g, 4.1 mmol) dissolved in methanol (10 ml) in, slowly adding concentrated sulfuric acid (3 ml), 70 °C heating 24 h. TLC monitoring display after the reaction. The reaction liquid concentrated, residue of ethyl acetate (20 ml) dissolved, saturated sodium bicarbonate solution to adjust pH to and 7 - 8, organic phase to saturated salt water (15 ml x 2) washing, drying with anhydrous sodium sulfate. Evaporate the solvent under reduced pressure. The residue by silica gel column chromatography (petroleum ether: ethyl acetate=50:1) purification to obtain compound 3 d (white solid, 456 mg, yield 44%).

References:

CN109748789,2019,A Location in patent:Paragraph 0125; 0127; 0129