ChemicalBook CAS DataBase List ethyl 3-bromo-5-methoxybenzoate

ethyl 3-bromo-5-methoxybenzoate synthesis

7synthesis methods

Product Name:ethyl 3-bromo-5-methoxybenzoate
CAS Number:56709-70-7
Molecular formula:C9H9BrO3
Molecular Weight:245.07

140472-69-1
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$19.00/250mg

74-88-4
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$15.00/10g

56709-70-7
52 suppliers
$250.00/1 G

Yield: 99%

Reaction Conditions:

with caesium carbonate in N,N-dimethyl-formamide at 0 - 20; for 12 h;

Steps:

4.2. 3-Bromo-5-methoxybenzoic acid methyl ester (16)
To a mixture of 3-bromo-5-hydroxybenzoic acid (2.5 g, 11.52 mmol) and cesium carbonate (7.5 g, 23.04 mmol) in DMF (20 mL) was added methyl iodide (4.08 g, 28.8 mmol) at 0 °C. After 10 min the ice bath was removed and the reaction allowed to warm to room temperature. The reaction mixture was stirred at room temperature for 12 h. The reaction was quenched with water (50 mL) and extracted with methyl t-butyl ether (30 mL x 3), combined organic layer was dried over sodium sulfate. Concentration of the organic layer in vacuo followed by silica gel column chromatographic purification of the resulting residue using hexaneas an eluent gave the product 16 as a brown syrup (2.8 g, 99 %): ¹H NMR (400 MHz, CDCl3) δ 7.75 (s, 1H), 7.48 (s, 1H), 7.23 (s, 1H), 3.91 (s, 3H), 3.83 (s, 3H); ¹³C NMR (100 MHz, CDCl3) δ 165.69, 160.23, 132.69, 124.91, 122.70, 122.18, 113.47, 55.76, 52.48; IR (Neat) ν_max 2952.04, 1727.14, 1678.80, 1286.68, 1049.20, 766.94 cm^-1; MS: m/z 245.2 (M + H)⁺.

References:

Bhatthula, Bharath kumar goud;Kanchani, Janardhan reddy;Arava, Veera reddy;Subha [Tetrahedron,2019,vol. 75,# 7,p. 874 - 887]

192810-12-1 Synthesis