Phosphorus oxychloride → 2-(1-Bromoethyl)-3-chloro-6-fluoroquinoxaline

Participants

Reaction Conditions

Reaction Steps

A heterogeneous mixture of 3-(1-bromoethyl)-7-fluoroquinoxalin-2(1H)-one (58.86 g, 217.1 mmol) and phosphorous oxychloride (198.8 ml, 2171 mmol) in a 1 L round bottom flask was stirred at 100° C. for 2 h. The mixture was hetereogeneous in the beginning of the reaction and then homogenesous black solution over 1 h. After 2 h, the mixture was cooled to rt and concentrated under reduced pressure. To the black residue was carefully added ice (˜400 ml) in portions and then water (200 ml) with stirring. The mixture was neutralized with NH4OH (200 ml) and ice (˜200 ml) with stirring. The resulting precipitate was collected by filtration, rinsed with water (1 L), and dried under high vacuum overnight to give 2-(1-bromoethyl)-3-chloro-6-fluoroquinoxaline (58.31 g, 92.8% yield) including 3-chloro-2-(1-chloroethyl)-6-fluoroquinoxaline as a brown solid.

Provenance & Evidence