Yield:58633-04-8 175 mg (74%)

Reaction Conditions:

with bromine in 1,4-dioxane;sodium hydroxide;

Steps:

1 Preparation of 4-Amino-3,5-dibromobenzonitrile STR15

EXAMPLE 1 Preparation of 4-Amino-3,5-dibromobenzonitrile STR15 To a stirred solution of 100 mg (0.847 mmoles) of p-aminobenzonitrile in 3.6 mL dioxane chilled in an ice-bath was added sequentially 356 μL (1.78 mmoles) of 5 N sodium hydroxide solution and 284 mg (1.78 mmoles) of bromine. The ice-water bath was removed and the reaction mixture was stirred further for 1.5 hours. After this time, 21.8 μL (0.423 mmoles) of bromine was added to drive the reaction to completion and stirring was continued for 10 minutes. The mixture was partitioned between ethyl acetate and ice-water and the organic phase was separated. It was washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated. Purification by plate layer chromatography using hexane-ethyl acetate (7:3) as eluant provided 175 mg (74%) of the entitled product. NMR(CDCl₃) δ: 5.1 (bs, 2H), 7.66 (s, 2H).

References:

US5192758,1993,A