4-bromo-N-(3,4-dimethoxyphenyl)benzamide synthesis

Yield:415691-56-4 72%

Reaction Conditions:

with pyridine in dichloromethane at 0 - 20;Inert atmosphere;

Steps:

2. General procedure 1: preparation of 3,4-dimethoxyanilides 1

General procedure: To a solution of 3,4-dimethoxyaniline (0.77 g, 5.0 mmol) in CH₂Cl₂ (8.0 mL) was added pyridine (4.0 mL, 50 mmol) and benzoyl chloride (0.70 g, 5.0 mmol) in CH₂Cl₂ (2.0 mL) at 0 °C, and stirred at room temperature under argon. The reaction was monitored by TLC. The resulting mixture was quenched with 1M HCl, extracted with CH₂Cl₂ (3 x 20 mL). The combined organic layer was washed with brine, dried over MgSO₄, and concentrated under vacuum. The crude compounds were purified with silica gel column chromatography (EtOAc : hexane = 1 : 2) and recrystallized from EtOAc/hexane to get the target anilide 1a (0.62 g, 48%).

References:

Fujimoto, Shigenobu;Matsumoto, Kenji;Iwata, Takayuki;Shindo, Mitsuru [Tetrahedron Letters,2017,vol. 58,# 10,p. 973 - 976] Location in patent:supporting information