Hydrogen Bromide → 1-Bromo-4-fluoro-2-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

A solution of 10 g of sodium nitrite in 30 ml of water were added with stirring at 0° C. to a suspension of 21.6 g of the product of Step B, 69 ml of 48% hydrobromic acid and 138 ml of water and the mixture was stirred at 0° C. for 10 minutes and then added with stirring to a solution of 30 g of cuprous bromide in 105 ml of 48% hydrobromic acid at 60° C. The mixture was stirred at 55°-60° C. for one hour and was poured into ice water. The mixture was extracted with isopropyl ether and the combined organic phases were dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and eluted with methylene chloride. The solution was evaporated to dryness and the residue was dried under reduced pressure to obtain 20.2 g of 2-nitro-4-fluoro-bromobenzene melting at 40°-41° C.

Provenance & Evidence