2-BROMO-3,4,5-TRIMETHOXY-BENZALDEHYDE synthesis

5synthesis methods

Product Name:2-BROMO-3,4,5-TRIMETHOXY-BENZALDEHYDE
CAS Number:35274-53-4
Molecular formula:C10H11BrO4
Molecular Weight:275.1

86-81-7 Synthesis

86-81-7
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35274-53-4
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$61.60/1g

Yield:35274-53-4 98%

Reaction Conditions:

with bromine in chloroform;water;Heating / reflux;

Steps:

1

The (4,4',5,6-tetramethoxybiphenyl-2,2'-diyl)dimethanol starting material was made as follows:To a stirred refluxing solution of 3,4,5-trimethoxybenzaldehyde (17.0 g, 86.6 mmol) in water (3 mL) and chloroform (100 mL) was added a solution of bromine (14.7 g, 92 mmol) in chloroform (30 mL) dropwise. The solution was heated under reflux overnight, cooled, washed with water (2 x 100 mL) and saturated aqueous sodium hydrogen carbonate (50 mL), dried over MgSO₄, filtered and evaporated. The residual orange oil (27 g) crystallised on standing. The solid was washed with petroleum ether, b.p. 40-60 ⁰C, to obtain 2-bromo-3,4,5-trimethoxybenzaldehyde as white crystals (23.4 g, 98%); m.p. 69 °C (literature value 69.5-71°C, see Brown, E.; Robin, J.-P.; Dhal, R. Tetrahedron 1982, 38, 2569-2579); NMR Spectrum δ_H (300 MHz, CDCl₃) 10.40 (1 H, s, 1-CHO), 7.29 (1 H, s, 6-H), 4.00 (3 H, s, OCH₃), 3.95 (3 H, s, OCH₃) and 3.93 (3 H, s, OCH₃); NMR Spectrum δ_c (75 MHz, CDCl₃) 56.6, 61.6, 106.9, 126.1, 128.1, 149.2, 150.3, 152.8, 189.2; v^/cin^"1 (thin film) 2940, 2843, 1685 (C=O), 1588, 1480, 1460, 1386, 1317, 1196, 1161, 1134, 1103 and 1002 (data in accordance with published values, see Brown, E.; Robin, J.-P.; Dhal, R. Tetrahedron 1982, 38, 2569-2579); R_f (hexane - ethyl acetate 4:1) 0.50.