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Lastly, the Sandemeyer reaction was carried out to obtain the desired bromo derivative Va in 25percent yield.
25%
With cis-nitrous acid; copper(I) bromide;
1. Para-anisidine was acylated at the amino center with acetic anhydride in dichloromethane and the product was obtained in 91 percent yield. Then, Friedel Craft's acyla- tion was carried out to get the hydroxyl acetophenone with acetyl chloride in the presence of anhydrous aluminium chloride in dichloromethane to give the product in 70percent yield. Nitration of acetanilide derivative was carried out with nitric acid in aqueous acetic acid to get the product in 45percent yield. Acetyl group of acetamido functionality was removed by refluxing in dilute hydrochloric acid for 2.5 h to get the aniline derivative in quantitative yield. Deamination was done by diazotization and treating the diazonium salt with ethanol to get the 3-nitro-2-hydroxyacetophenone. The nitro group was reduced by heating the reaction mixture in ethyl acetate with tin in hydrochloric acid resulting in the formation of corresponding amino compound. Lastly, Sandemeyer reaction was carried out to get the desired bromo derivative Va in 25percent yield.
270 g of 4- (phenylbutoxy) benzoic acid was added, 270 g of thionyl chloride was added and incubated at 50 C for 3 hours. After completion of the reaction, the unreacted thionyl chloride was recovered under reduced pressure. Nitrogen blowing into the thiophene chloride. Cooled to room temperature by adding 270 g of dichloromethane. Weigh 151 g of 3-amino-2-hydroxyacetophenone in 200 g of methylene chloride, 160 g of pyridine was added, and a solution of 4- (phenylbutoxy) benzoyl chloride in methylene chloride was added dropwise to the ice bath. The temperature is not more than 10 , dripping finished, 10 incubation reaction 2h, after the end of the reaction, adding to the reaction system dilute hydrochloric acid, adjust the pH to 2-3, liquid, methyl chloride layer washed to neutral, anhydrous Dried over sodium sulfate, filtered and concentrated to give a reddish brown solid, petroleum ether: ethyl acetate = 1: 1 recrystallization to give 334 g, yield 84%.
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