* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Iron powder (5.69 g, 102.0 mmol) was added to a solution of l-(4-bromo-2- nitropheny ethanone (62, 4.16 g, 17.0 mmol) in 30 mL of acetic acid and the resulting suspension was heated to 90 °C for 1 hour. After cooling to room temperature the reaction mixture was diluted with brine and EtOAc and adjusted to pH 10 by the addition of 3N aqueous NaOH. The mixture was filtered and the filtrate was extracted 3x with EtOAc. The combined organic phases were dried with Na2S04, filtered and the filtrate concentrated under vacuum to give of 1 -(2-amino-4- bromophenyl)ethanone (63, 3.1 g, 14.4 mmol, 85percent). MS: 214.0 m/z (M+H)+.
Reference：
[1] Liebigs Annalen der Chemie, 1990, # 2, p. 205 - 206
[2] Patent: WO2012/162254, 2012, A1, . Location in patent: Page/Page column 152
2
[ 1262802-05-0 ]
[ 90004-94-7 ]
Reference：
[1] Chemistry - A European Journal, 2010, vol. 16, # 46, p. 13590 - 13593
[2] Journal of Organic Chemistry, 2013, vol. 78, # 12, p. 5932 - 5948
Iron powder (5.69 g, 102.0 mmol) was added to a solution of l-(4-bromo-2- nitropheny ethanone (62, 4.16 g, 17.0 mmol) in 30 mL of acetic acid and the resulting suspension was heated to 90 C for 1 hour. After cooling to room temperature the reaction mixture was diluted with brine and EtOAc and adjusted to pH 10 by the addition of 3N aqueous NaOH. The mixture was filtered and the filtrate was extracted 3x with EtOAc. The combined organic phases were dried with Na2S04, filtered and the filtrate concentrated under vacuum to give of 1 -(2-amino-4- bromophenyl)ethanone (63, 3.1 g, 14.4 mmol, 85%). MS: 214.0 m/z (M+H)+.
With sulfuric acid; water; acetic acid; for 2.0h;Reflux;
Diethyl 2-(4- bromo-2-ni trobenzoyl)malonate 61 was dissolved in 15 mL of acetic acid and 15 mL of 20% aqueous H2S04 and the resulting solution was refluxed for 2 hours. After cooling to room temperature the solution was adjusted to pH 10 by the addition of 3N aqueous NaOH and extracted 3x with EtOAc. The combined organic phases were dried with Na2S04, filtered, and the filtrate concentrated under vacuum. The resulting residue was purified by silica gel chromatography eluting with hexane/EtOAc to give l-(4-bromo-2-nitrophenyl)ethanone (62, 4.16 g, 17.0 mmol, 42%, 2 steps) as a tan solid. MS: 243.9 m/z (M+H)+.
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