Water → 2-Bromo-1,3,5-trimethoxybenzene

Participants

Reaction Conditions

Reaction Steps

KM03 Dissolve 1,3,5-trimethoxybenzene (10.0 g, 59.46 mmol) in anhydrous dichloromethane (100 mL), cool the reaction mixture to −78° C., add dropwise bromine (3.0 mL, 59.44 mmol) stir the mixture for 1 h between −70° C. and −40° C. Warm up the solution to 0° C. and add water. Separate layers and extract the aqu. layer with EtAOc (3 times). Wash combined organic layer with water and brine and dry it with Na2SO4. Remove solvent and purify the crude product by recrystallization from hot EtOAc and cyclohexane to obtain 2-Bromo-1,3,5-trimethoxy-benzene (48) as a white solid (8.84 g, 60%). 1H NMR (400 MHz, CDCl3): 3.80 (s, 3 H); 3.86 (s, 6 H); 6.15 (s, 2 H).

Provenance & Evidence