3-BroMo-4-[2-(diMethylaMino)ethoxy]benzaldehyde synthesis

Yield:938294-99-6 77%

Reaction Conditions:

Stage #1: 3-bromo-4-hydroxybenzylaldehydewith potassium carbonate in N,N-dimethyl-formamide at 80; for 0.5 h;
Stage #2: (2-chloroethyl)dimethylamine hydrochloride in N,N-dimethyl-formamide at 80; for 18 h;

Steps:

11 Preparation of 3-Bromo-4-(2-(dimethylamino)ethoxy)benzaldehyde (2)

A mixture of 3-bromo-4-hydroxybenzaldehyde (1, 1.00 g, 5 mmol) in DMF (15 mL) was treated with K₂CO₃ (2.07 g, 15.0 mmol) and heated at 80° C. for 30 min. 2-Chloro-N,N-dimethylethanamine hydrochloride (0.864 g, 6.00 mmol) was added and the mixture was heated at 80° C. for 18 h. The mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography eluting with 0-2% MeOH in CH₂Cl₂ to afford the title compound (1.05 g, 77%) as light brown oil.

References:

US2014/140956,2014,A1 Location in patent:Paragraph 0686; 0687