ChemicalBook CAS DataBase List methyl 4-bromo-3,5-dimethoxybenzoate

methyl 4-bromo-3,5-dimethoxybenzoate synthesis

10synthesis methods

Product Name:methyl 4-bromo-3,5-dimethoxybenzoate
CAS Number:26050-64-6
Molecular formula:C10H11BrO4
Molecular Weight:275.1

16534-12-6
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26050-64-6
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Yield: 92%

Reaction Conditions:

with potassium carbonate;dimethyl sulfate in acetone for 24 h;Reflux;Inert atmosphere;

Steps:

1 4.1.1 Methyl 4-bromo-3,5-dimethoxybenzoate (4)
To the stirred solution of 4-bromo-3,5-dihydroxybenzoic acid (3) 24.0 g, 0.103 mol) in dry acetone (100 mL), K₂CO₃ (20.0 g, 0.145 mol), and dimethyl sulfate (20 mL, 0.309 mol) was added with caution.
The reaction mixture was refluxed for 24 h.
On completion of reaction (TLC control) the reaction mixture was filtered off and the filtrate was concentrated in vacuo.
Recrystallization from ethanol afforded methyl 4-bromo-3,5-dimethoxybenzoate 4 as colorless prisms. (24.5 g, 92%) R_f=0.65; Mp 124-126 °C (lit.34b 100-102 °C) (ν_max (KBr): 1723, 1601, 1588 (C=C) cm^-1. ¹H NMR (300 MHz, CDCl₃) δ 6.72 (2H, s, H-2, H-6), 3.78 (3H, s, COOCH₃), 3.62 (6H, s, OCH₃) ppm. ¹³C NMR δ (CDCl₃): 179.2 (C=O), 157.7 (C-3,5), 134.5 (C-1), 125.3 (C-4), 113.2 (C-2,6), 58.3 (COCH₃), 63.2 (OCH₃) ppm. Anal. Calcd for C₁₀H₁₁BrO₄: C, 43.44; H, 4.02; Found: C, 43.32; H, 4.01; GC-MS m/z 273.9, 275.9.