Ammonium Chloride → HCID 19825386, compound

Participants

Reaction Steps

To a solution of 100 g (4.52 mmol) of 5-bromo-2-chlorobenzyl alcohol in dry dichloromethane (20 ml) were added 675 mg (5.42 mmol) of 2-methoxyethoxymethyl chloride and 1.20 ml (6.89 mmol) of N,N-diisopropylethylamine in an atmosphere of argon, and the mixture was allowed to react at room temperature for 18 hours. To the reaction solution at 0° C. was a added saturated aqueous solution of ammonium chloride followed by extraction with ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with dichloromethane-hexane (1:5) yielded 1.23 g (3.98 mmol) of 4-bromo-1-chloro-2-(2-methoxyethoxymethoxymethyl)benzene.

Provenance & Evidence