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The general procedure for the synthesis of 1-bromo-5-nitronaphthalene from 1-nitronaphthalene is as follows: 77.5 g (0.485 mol) of bromine was added slowly and dropwise to a stirred mixture of 86 g (0.5 mol) of 1-nitronaphthalene and 0.8-1.0 g of reduced iron powder over a period of 30 min, while the reaction temperature was maintained at 80-85°C. The reaction was carried out in the following manner. After about one hour, the reaction mixture crystallized directly when gas escape ceased. Subsequently, one crystallization was carried out with ethanol and two more with Sorit A from acetone. An average of 52.0 g of a fine yellow needle-like product was obtained with a melting point of 121-122°C (41% yield); the literature reports a melting point of 122.5°C.

[1] New Journal of Chemistry, 2005, vol. 29, # 4, p. 579 - 586
[2] Chemistry Letters, 2015, vol. 44, # 6, p. 743 - 745
[3] Angewandte Chemie - International Edition, 2008, vol. 47, # 32, p. 6062 - 6064
[4] Journal of Organic Chemistry, 2017, vol. 82, # 7, p. 3873 - 3879
[5] Journal of Organic Chemistry, 1949, vol. 14, p. 111,114